Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2018; 29(12): 1552-1571
DOI: 10.1055/s-0037-1610126
DOI: 10.1055/s-0037-1610126
account
Diversity-Oriented Synthesis of Natural Products via Gold-Catalyzed Cascade Reactions
Yueqing Gu
a
State Key Laboratory of Chemical Oncogenomics, Key Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen 518055, P. R. of China Email: gongjx@pku.edu.cn
,
Ceheng Tan
a
State Key Laboratory of Chemical Oncogenomics, Key Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen 518055, P. R. of China Email: gongjx@pku.edu.cn
,
Jianxian Gong*
a
State Key Laboratory of Chemical Oncogenomics, Key Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen 518055, P. R. of China Email: gongjx@pku.edu.cn
,
a
State Key Laboratory of Chemical Oncogenomics, Key Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen 518055, P. R. of China Email: gongjx@pku.edu.cn
b
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science, College of Chemistry and Molecular Engineering, and Peking-Tsinghua Center for Life Sciences, Peking University, Beijing 100871, P. R. of China Email: zyang@pku.edu.cn
› Author Affiliations
Further Information
Publication History
Received: 10 March 2018
Accepted after revision: 05 April 2018
Publication Date:
16 May 2018 (online)
Abstract
This account describes our group’s latest research in the field of diversity-oriented synthesis of natural products via gold-catalyzed cascade reactions. We present two general strategies based on gold-catalyzed cycloisomerization: a gold-catalyzed cascade reaction of 1,7-diynes and a pinacol-terminated gold-catalyzed cascade reaction. We highlight our development of synthetic methods for the construction of biologically active natural products by using these two strategies.
1 Introduction
2 Gold-Catalyzed Cascade Reactions of 1,7-Diynes
2.1 Collective Synthesis of C15 Oxygenated Drimane-Type Sesquiterpenoids
2.2 Synthesis of Left-Wing Fragment of Azadirachtin I
2.3 Collective Synthesis of Cladiellins
3 Pinacol-Terminated Gold-Catalyzed Cascade Reaction
3.1 Asymmetric Formal Total Synthesis of (+)-Cortistatins
3.2 Total Synthesis of Orientalol F
3.3 Asymmetric Total Synthesis of (–)-Farnesiferol C
4 Summary and Outlook
-
References
- 1a Allred TK. Manoni F. Harran PG. Chem. Rev. 2017; 117: 11994
- 1b Ghogare AA. Greer A. Chem. Rev. 2016; 116: 9994
- 2 Newman DJ. Cragg GM. J. Nat. Prod. 2012; 75: 311
- 3 Zhang Y. Gong J.-X. Yang Z. Chem. Rec. 2014; 14: 606
- 5 Bond GC. Sermon PA. Webb G. Buchanan DA. Wells PB. Chem. Soc., Chem. Commun. 1973; 444b
- 6 Ito Y. Sawamura M. Hayashi T. J. Am. Chem. Soc. 1986; 108: 6405
- 7 Hashmi AS. K. Schearz L. Choi J.-H. Frost TM. Angew. Chem. Int. Ed. 2000; 39: 2285
- 8a Luzung MR. Markham JP. Toste FD. J. Am. Chem. Soc. 2004; 126: 10858
- 8b Mamane V. Gress T. Krause H. Fürstner A. J. Am. Chem. Soc. 2004; 126: 8654
- 8c Nieto-Oberhuber C. Munoz MP. Bunuel E. Nevado C. Cardenas DJ. Echavarren AM. Angew. Chem. Int. Ed. 2004; 43: 2402
- 8d Zhang L. Kozmin SA. J. Am. Chem. Soc. 2004; 126: 11806
- 9a Miró J. del Pozo C. Chem. Rev. 2016; 116: 11924
- 9b Dorel R. Echavarren AM. Chem. Rev. 2015; 115: 9028
- 9c Corma A. Leyva-Pérez A. Sabater MJ. Chem. Rev. 2011; 111: 1657
- 9d Krause N. Winter C. Chem. Rev. 2011; 111: 1994
- 9e Arcadi A. Chem. Rev. 2008; 108: 3266
- 9f Jiménez-Núñez E. Echavarren AM. Chem. Rev. 2008; 108: 3326
- 9g Li Z. Brouwer C. He C. Chem. Rev. 2008; 108: 3239
- 9h Gorin DJ. Sherry BD. Toste FD. Chem. Rev. 2008; 108: 3351
- 9i Hashmi AS. K. Chem. Rev. 2007; 107: 3180
- 9j Hashmi AS. K. Rudolph M. Chem. Soc. Rev. 2008; 37: 1766
- 9k Marion N. Nolan SP. Chem. Soc. Rev. 2008; 37: 1776
- 9l Fürstner A. Chem. Soc. Rev. 2009; 38: 3208
- 9m Yang W. Hashmi AS. K. Chem. Soc. Rev. 2014; 43: 2941
- 9n Asiri AM. Hashmi AS. K. Chem. Soc. Rev. 2016; 45: 4471
- 9o Rudolph M. Hashmi AS. K. Chem. Soc. Rev. 2012; 41: 2448
- 9p Lu B.-L. Dai L. Shi M. Chem. Soc. Rev. 2012; 41: 3318
- 9q Zi W. Toste D. Chem. Soc. Rev. 2016; 45: 4567
- 9r Qian D. Zhang J. Chem. Soc. Rev. 2015; 44: 677
- 9s Bandini M. Chem. Soc. Rev. 2011; 40: 1358
- 9t Abu Sohel SM. Liu R.-S. Chem. Soc. Rev. 2009; 38: 2269
- 9u Boorman TC. Larrosa I. Chem. Soc. Rev. 2011; 40: 1910
- 9v Liu L. Zhang J. Chem. Soc. Rev. 2016; 45: 506
- 9w Xie J. Pan C. Abdukader A. Zhu C. Chem. Soc. Rev. 2014; 43: 5245
- 9x Pflästerer D. Hashmi AS. K. Chem. Soc. Rev. 2016; 45: 1331
- 9y Harris RJ. Widenhoefer RA. Chem. Soc. Rev. 2016; 45: 4533
- 9z Sugimoto K. Matsuya Y. Tetrahedron 2017; 58: 4420
- 10 Oh CH. Kim A. Synlett 2008; 777
- 11a Hashmi AS. K. Wölfle M. Ata F. Frey W. Rominger F. Synthesis 2010; 2297
- 11b Hashmi AS. K. Ghanbari M. Rudolph M. Rominger F. Chem. Eur. J. 2012; 18: 8113
- 12 Rao W. Koh MJ. Kothandaraman P. Chan PW. H. J. Am. Chem. Soc. 2012; 134: 10811
- 13 Rao W. Susanti D. Ayers BJ. Chan PW. H. J. Am. Chem. Soc. 2015; 137: 6350
- 14 Chen M. Liu J. Wang L. Zhou X. Liu Y. Chem. Commun. 2013; 8650
- 15 Tokimizu Y. Oishi S. Fujii N. Ohno H. Angew. Chem. Int. Ed. 2015; 54: 7862
- 16 Shi H. Fang L. Tan C. Shi L. Zhang W. Li C.-C. Luo T. Yang Z. J. Am. Chem. Soc. 2011; 133: 14944
- 17a Appel HH. Scientia (Valparaiso) 1948; 15: 31
- 17b Appel HH. Rotman B. Thornton F. Scientia (Chile) 1956; 23: 19
- 18a Jansen BJ. M. de Groot A. Nat. Prod. Rep. 1991; 8: 309
- 18b Jansen BJ. M. de Groot A. Nat. Prod. Rep. 2004; 21: 449
- 19 Chiang H.-C. Wu D.-P. Cherng IW. Ueng CH. Phytochemistry 1995; 39: 613
- 20 Chiu K.-Y. Wu C.-C. Chia C.-H. Hsu S.-L. Tzeng Y.-M. Cancer Lett. 2016; 373: 174
- 21 Yeh C.-T. Huang W.-C. Rao YK. Ye M. Lee W.-H. Wang L.-S. Tzeng DT. W. Wu C.-H. Shieh Y.-S. Huang C.-YF. Chen Y.-J. Hsiao M. Wu AT. H. Yang Z. Tzeng Y.-M. Carcinogenesis 2013; 34: 2918
- 22a Erkel G. Lorenzen K. Anke T. Velten R. Gimenez A. Steglich W. Z. Naturforsch., C. 1995; 50: 1
- 22b Velten R. Klostermeyer D. Steffan B. Steglich W. Kuschel A. Anke T. J. Antibiot. 1994; 47: 1017
- 22c Kuschel A. Anke T. Velten R. Klostermeyer D. Steglich W. König B. J. Antibiot. 1994; 47: 733
- 23 Toyota M. Ooiso Y. Kusuyama T. Asakawa Y. Phytochemistry 1994; 35: 1263
- 24 Tabata N. Tomoda H. Masuma R. Iwai Y. Omura S. J. Antibiot. 1995; 48: 53
- 25a Watanabe H. Furuuchi T. Yamaguchi T. Kitahara T. Org. Lett. 1999; 1: 1079
- 25b Watanabe H. Yamaguchi T. Furuuchi T. Kitahara T. Tetrahedron Lett. 2001; 42: 917
- 26a Jauch J. Angew. Chem. Int. Ed. 2000; 39: 2764
- 26b Suzuki Y. Nishimaki R. Ishikawa M. Murata T. Takao K.-I. Tadano K.-I. J. Org. Chem. 2000; 65: 8595
- 26c Suzuki Y. Ohara A. Sugaya K. Takao K.-I. Tadano K.-I. Tetrahedron 2001; 57: 7291
- 26d Jauch J. Eur. J. Org. Chem. 2001; 473
- 26e Jauch J. Synlett 2001; 87
- 26f Jauch J. Wallner C. Herdtweck E. Eur. J. Org. Chem. 2003; 3060
- 26g Ishihara J. Yamamoto Y. Kanoh N. Murai A. Tetrahedron Lett. 1999; 40: 4387
- 27 Liu H.-J. Browne EN. C. Chew SY. Can. J. Chem. 1988; 66: 2345
- 28 González DF. Brand JP. Waser J. Chem. Eur. J. 2010; 16: 9457
- 29a Tan Q.-G. Luo X.-D. Chem. Rev. 2011; 111: 7437
- 29b Jain DC. Tripathi AK. Phytother. Res. 1993; 7: 327
- 29c Roy A. Saraf S. Biol. Pharm. Bull. 2006; 29: 191
- 30a Ley SV. Denholm AA. Wood A. Nat. Prod. Rep. 1993; 10: 109
- 30b Mordue Luntz AJ. Simmonds MS. J. Ley SV. Blaney WM. Mordue W. Nasiruddin M. Nisbet A. J. Pestic. Sci. 1998; 54: 277
- 30c Morgan ED. Bioorg. Med. Chem. 2009; 17: 4096
- 31a Govindachari TR. Sandhya G. Raj SP. G. J. Nat. Prod. 1992; 55: 596
- 31b Govindachari TR. Narasimhan NS. Suresh G. Partho PD. Gopalakrishnan G. Krishnakumari GN. J. Chem. Ecol. 1995; 21: 1585
- 31c Suresh G. Gopalakrishnan G. Wesley SD. Singh ND. P. Malathi R. Rajan SS. J. Agric. Food Chem. 2002; 50: 4484
- 31d Lee SM. Klocke JA. Balandrin MF. Tetrahedron Lett. 1987; 28: 3543
- 32 Morgan ED. Butterworth JH. Chem. Commun. 1968; 23
- 33a Veitch GE. Boyer A. Ley SV. Angew. Chem. Int. Ed. 2008; 47: 9402
- 33b Haag D. Chen X.-T. Fraser-Reid B. Chem. Commun. 1998; 2577
- 33c Nakagawa D. Miyashita M. Tanino K. Tetrahedron 2010; 51: 2771
- 34a Denholm AA. Jennens L. Ley SV. Wood A. Tetrahedron 1995; 51: 6591
- 34b Veitch GE. Beckmann E. Burke BJ. Boyer A. Maslen SL. Ley SV. Angew. Chem. Int. Ed. 2007; 46: 7629
- 34c Veitch GE. Beckmann E. Burke BJ. Boyer A. Ayats C. Ley SV. Angew. Chem. Int. Ed. 2007; 46: 7633
- 34d Veitch GE. Boyer A. Ley SV. Angew. Chem. Int. Ed. 2008; 47: 9402
- 34e Ley SV. Abad-Somovilla A. Anderson JC. Ayats C. Bänteli R. Beckmann E. Boyer A. Brasca MG. Brice A. Broughton HB. Burke BJ. Cleator E. Craig D. Denholm AA. Denton RM. Durand-Reville T. Gobbi LB. Göbel M. Gray BL. Grossmann RB. Gutteridge CE. Hahn N. Harding SL. Jennens DC. Jennens L. Lovell PJ. Lovell HJ. de la Puente ML. Kolb HC. Koot W.-J. Maslen SL. McCusker CF. Mattes A. Pape AR. Pinto A. Santafianos D. Scott JS. Smith SC. Somers AQ. Spilling CD. Stelzer F. Toogood PL. Turner RM. Veitch GE. Wood A. Zumbrunn C. Chem. Eur. J. 2008; 14: 10683
- 34f Jauch J. Angew. Chem. Int. Ed. 2008; 47: 34
- 34g Heasley B. Eur. J. Org. Chem. 2011; 19
- 35a Kanoh N. Ishihara J. Yamamoto Y. Murai A. Synthesis 2000; 1878
- 35b Fukuzaki T. Kobayashi S. Hibi T. Ikuma Y. Ishihara J. Kanoh N. Murai A. Org. Lett. 2002; 4: 2877
- 36a Nicolaou KC. Follmann M. Roecker AJ. Hunt KW. Angew. Chem. Int. Ed. 2002; 41: 2103
- 36b Nicolaou KC. Roecker AJ. Follmann M. Baati R. Angew. Chem. Int. Ed. 2002; 41: 2107
- 36c Nicolaou KC. Roecker AJ. Monenschein H. Guntupalli P. Follmann M. Angew. Chem. Int. Ed. 2003; 42: 3637
- 36d Nicolaou KC. Sasmal PK. Roecker AJ. Sun X.-W. Mandal S. Converso A. Angew. Chem. Int. Ed. 2005; 44: 3443
- 36e Nicolaou KC. Sasmal PK. Koftis TV. Converso A. Loizidou E. Kaiser F. Roecker AJ. Dellios CC. Sun X.-W. Petrovic G. Angew. Chem. Int. Ed. 2005; 44: 3447
- 37 Watanabe H. Mori N. Itoh D. Kitahara T. Mori K. Angew. Chem. Int. Ed. 2007; 46: 1512
- 38a Nicolai S. Erard S. González FG. Waser J. Org. Lett. 2010; 12: 384
- 38b Nicolai S. Piemontesi C. Waser J. Angew. Chem. Int. Ed. 2011; 50: 4680
- 38c Nicolai S. Waser J. Org. Lett. 2011; 13: 6324
- 38d Nicolai S. Sedigh-Zadeh R. Waser J. J. Org. Chem. 2013; 78: 3783
- 39 Deguest G. Bischoff L. Fruit C. Marsais F. Org. Lett. 2007; 9: 1165
- 40 Schreiber SL. Liew W.-F. Tetrahedron Lett. 1983; 24: 2363
- 41a Crump RA. N. C. Fleming I. Urch CJ. J. Chem. Soc., Perkin Trans. 1 1994; 701
- 41b Dunn TB. Ellis JM. Kofink CC. Manning JR. Overman LE. Org. Lett. 2009; 11: 5658
- 42 Nelson SG. Peelen TJ. Wan Z. J. Am. Chem. Soc. 1999; 121: 9742
- 43a Kennard O. Watson DG. di Sanseverino LR. Tursch B. Bosmans R. Djerassi C. Tetrahedron 1968; 2879
- 43b Kennard O. Watson DG. Riva di Sanseverino L. Acta Crystallogr., Sect. B: Struct. Sci. 1970; 26: 1038
- 44a Bernardelli P. Paquette LA. Heterocycles 1998; 49: 531
- 44b Ellis JM. Crimmins MT. Chem. Rev. 2008; 108: 5278
- 44c Welford AJ. Collins I. J. Nat. Prod. 2011; 74: 2318
- 45a Sharma P. Alam M. J. Chem. Soc., Perkin Trans. 1 1988; 2537
- 45b Alam M. Sharma P. Zektzer AS. Martin GE. Ji X. van der Helm DJ. J. Org. Chem. 1989; 54: 1896
- 46a Su J.-H. Huang H.-C. Chao C.-H. Yan LY. Wu Y.-C. Wu C.-C. Sheu J.-H. Bull. Chem. Soc. Jpn. 2005; 78: 877
- 46b Hassan HM. Khanfar MA. Elnagar AY. Mohammed R. Shaala LA. Youssef DT. A. Hifnawy MS. El Sayad KA. J. Nat. Prod. 2010; 73: 848
- 47a MacMillan DW. C. Overman LE. J. Am. Chem. Soc. 1995; 117: 10391
- 47b Overman LE. Pennington LD. Org. Lett. 2000; 2: 2683
- 47c MacMillan DW. C. Overman LE. Pennington LD. J. Am. Chem. Soc. 2001; 123: 9033
- 47d Gallou F. MacMillan DW. C. Overman LE. Paquette LA. Pennington LD. Yang J. Org. Lett. 2001; 3: 135
- 48a Paquette LA. Moradei OM. Bernardelli P. Lange T. Org. Lett. 2000; 2: 1875
- 48b Friedrich D. Doskotch RW. Paquette LA. Org. Lett. 2000; 2: 1879
- 48c Bernardelli P. Moradei OM. Friedrich D. Yang J. Gallou F. Dyck BP. Doskotch RW. Lange T. Paquette LA. J. Am. Chem. Soc. 2001; 123: 9021
- 48d Crimmins MT. Brown BH. J. Am. Chem. Soc. 2004; 126: 10264
- 48e Crimmins MT. Ellis JM. J. Am. Chem. Soc. 2005; 127: 17200
- 48f Crimmins MT. Brown BH. Plake HR. J. Am. Chem. Soc. 2006; 128: 1371
- 48g Crimmins MT. Michael Ellis J. J. Org. Chem. 2008; 73: 1649
- 48h Crimmins MT. Mans MC. Rodríguez A. D. Org. Lett. 2010; 12: 5028
- 48i Crimmins MT. Stauffer CS. Mans MC. Org. Lett. 2011; 13: 4890
- 48j Molander GA. St Jean DJ. Jr. Haas J. J. Am. Chem. Soc. 2004; 126: 1642
- 48k Molander GA. Czakó B. St Jean DJ. Jr. J. Org. Chem. 2006; 71: 1172
- 48l Kim H. Lee H. Kim J. Kim S. Kim D. J. Am. Chem. Soc. 2006; 128: 15851
- 48m Clark JS. Hayes ST. Wilson C. Gobbi L. Angew. Chem. Int. Ed. 2007; 46: 437
- 48n Clark JS. Berger R. Hayes ST. Thomas LH. Morrison AJ. Gobbi L. Angew. Chem. Int. Ed. 2010; 49: 9867
- 48o Clark JS. Berger R. Hayes ST. Senn HM. Farrugia LJ. Thomas LH. Morrison AJ. Gobbi L. J. Org. Chem. 2013; 78: 673
- 48p Becker J. Bergander K. Fröhlich R. Hoppe D. Angew. Chem. Int. Ed. 2008; 47: 1654
- 48q Campbell MJ. Johnson JS. J. Am. Chem. Soc. 2009; 131: 10370
- 48r Campbell MJ. Johnson JS. Synthesis 2010; 2841
- 48s Wang B. Ramirez AP. Slade JJ. Morken JP. J. Am. Chem. Soc. 2010; 132: 16380
- 49 Marshall JA. Grant CM. J. Org. Chem. 1999; 64: 696
- 50 Morales MR. Mellem KT. Myers AG. Angew. Chem. Int. Ed. 2012; 51: 4568
- 51 Midland MM. Tramontano A. Kazubski A. Graham RS. Tsai DJ. S. Cardin DB. Tetrahedron 1984; 40: 1371
- 53 Sun T.-W. Ren W.-W. Xiao Q. Tang Y.-F. Zhang Y.-D. Li Y. Meng F.-K. Liu Y.-F. Zhao M.-Z. Xu L.-M. Chen J.-H. Yang Z. Chem. Asian J. 2012; 7: 2321
- 54a Caglioti L. Naef H. Arigoni D. Jeger O. Helv. Chim. Acta 1959; 42: 2557
- 54b Schenk H. Driessen RA. J. de Gelder R. Goubitz K. Nieboer H. Bruggemann-Rotgans IE. M. Diepenhorst P. Croat. Chem. Acta 1999; 72: 593
- 54c Zhang C. Ondeyka J. Herath K. Jayasuriya H. Guan Z. Zink DL. Dietrich L. Burgess B. Ha SN. Wang J. Singh SB. J. Nat. Prod. 2011; 74: 329
- 54d Lua C.-H. Liu S.-S. Wang J.-Y. Wang M.-Z. Shen Y.-M. Helv. Chim. Acta 2014; 97: 334
- 54e Han J.-J. Bao L. Tao Q.-Q. Yao Y.-J. Liu X.-Z. Yin W.-B. Liu H.-W. Org. Lett. 2015; 17: 2538
- 54f Sharma P. Alam M. J. Chem. Soc., Perkin Trans. 1 1988; 2537
- 54g Ospina CA. Rodriguez AD. Ortega-Barria E. Capson TL. J. Nat. Prod. 2003; 66: 357
- 55a Lipshutz BH. Chem. Rev. 1986; 86: 795
- 55b Kappe CO. Murphree SS. Padwa A. Tetrahedron 1997; 53: 14179
- 55c Orugunty RS. Ghiviriga I. Abboud KA. Battiste MA. Wright DL. J. Org. Chem. 2004; 69: 570
- 55d Oblak EZ. Wright DL. Org. Lett. 2011; 13: 2263
- 55e Xue YP. Li WD. J. Org. Chem. 2011; 76: 57
- 55f Yamada Y. Sanjoh H. Iguchi K. J. Chem. Soc., Chem. Commun. 1976; 997
- 55g Warrener RN. Russell RA. Tan RY. S. Tetrahedron Lett. 1987; 1585
- 55h Carless HA. J. Oak OZ. J. J. Chem. Soc., Chem. Commun. 1991; 61
- 55i Kinder FR. Bair KW. J. Org. Chem. 1994; 59: 6965
- 55j Padwa A. Kassir JM. Semones MA. Weingarten MD. J. Org. Chem. 1995; 60: 53
- 55k Weingarten MD. Prein M. Price AT. Snyder JP. Padwa A. J. Org. Chem. 1997; 62: 2001
- 55l Warrener RN. Schultz AC. Butler DN. Wang S. Mahadevan IB. Russell RA. Chem. Commun. 1997; 1023
- 55m Padwa A. Price AT. J. Org. Chem. 1998; 63: 556
- 55n Ullman EF. Milks JE. J. Am. Chem. Soc. 1962; 84: 1315
- 55o Feldman KS. Tetrahedron Lett. 1983; 24: 5585
- 55p Lopez F. Castedo L. Mascarenas JL. Org. Lett. 2000; 2: 1005
- 55q Burns NZ. Witten MR. Jacobsen EN. J. Am. Chem. Soc. 2011; 133: 14578
- 55r Witten MR. Jacobsen EN. Angew. Chem. Int. Ed. 2014; 53: 5912
- 55s Orue A. Uria U. Reyes E. Carrillo L. Vicario JL. Angew. Chem. Int. Ed. 2015; 54: 3043
- 55t Cho SY. Lee JC. Cha JK. J. Org. Chem. 1999; 64: 3394
- 55u Xiong H. Huang J. Ghosh SK. Hsung RP. J. Am. Chem. Soc. 2003; 125: 12694
- 55v Harmata M. Ghosh SK. Hong X. Wacharasindhu S. Kirchhoefer P. J. Am. Chem. Soc. 2003; 125: 2058
- 55w Huang J. Hsung RP. J. Am. Chem. Soc. 2005; 127: 50
- 55x Kitagaki S. Anada M. Kataoka O. Matsuno K. Umeda C. Watanabe N. Hashimoto S. J. Am. Chem. Soc. 1999; 121: 1417
- 55y Shu X.-Z. Zhao S.-C. Ji KG. Zheng Z.-J. Liu X.-Y. Liang T.-M. Eur. J. Org. Chem. 2009; 117
- 55z Kusama H. Ishida K. Funami H. Iwasawa N. Angew. Chem. Int. Ed. 2008; 47: 4903
- 55aa Obradors C. Echavarren AM. Chem. Eur. J. 2013; 19: 3547
- 55ab Oonishi Y. Yokoe T. Hosotani A. Sato Y. Angew. Chem. Int. Ed. 2014; 53: 1135
- 56a Cho YS. Kim HY. Cha JH. Pae AN. Koh HY. Choi JH. Chang MH. Org. Lett. 2002; 4: 2025
- 56b Hegemann K. Frohlich R. Haufe G. Eur. J. Org. Chem. 2004; 2181
- 56c Fawcett J. Griffith GA. Percy JM. Uneyama E. Org. Lett. 2004; 6: 1277
- 56d Xiao Q. Ren W.-W. Chen Z.-X. Sun T.-W. Li Y. Ye Q.-D. Gong J.-X. Meng F.-K. You L. Liu Y.-F. Zhao M.-Z. Xu L.-M. Shan Z.-H. Shi Y. Tang Y.-F. Chen J.-H. Yang Z. Angew. Chem. Int. Ed. 2011; 50: 7373
- 57 Markham JP. Staben ST. Toste FD. J. Am. Chem. Soc. 2005; 127: 9708
- 58 Jiménez-Núñez E. Claverie CK. Nieto-Oberhuber C. Echavarren AM. Angew. Chem. Int. Ed. 2006; 45: 5452
- 59 Kirsch SF. Binder JT. Crone B. Duschek A. Haug TT.. Liébert C. Menz H. Angew. Chem. Int. Ed. 2007; 46: 2310
- 60 Huang X. Zhang L. J. Am. Chem. Soc. 2007; 129: 6398
- 61 Tang J.-M. Bhunia S. Abu Sohel SM. Lin M.-Y. Liao H.-Y. Datta S. Das A. Liu R.-S. J. Am. Chem. Soc. 2007; 129: 15677
- 62 Fu J. Gu Y. Yuan H. Luo T. Li S. Lan Y. Gong J. Yang Z. Nat. Commun. 2015; 6: 8617
- 63a Barluenga J. Diéguez A. Fernández A. Rodríguez F. Fañanás FJ. Angew. Chem. Int. Ed. 2006; 45: 2091
- 63b Barluenga J. Fernández A. Diéguez A. Rodríguez F. Fañanás FJ. Chem. Eur. J. 2009; 15: 11660
- 63c Krauter CM. Hashmi AS. K. Pernpointner M. ChemCatChem 2010; 2: 1226
- 64a Crone B. Kirsch SF. Chem. Eur. J. 2008; 14: 3514
- 64b Song ZL. Fan CA. Tu YQ. Chem. Rev. 2011; 111: 7523
- 64c Zhang XM. Tu YQ. Zhang FM. Chen ZH. Wang SH. Chem. Soc. Rev. 2017; 46: 2272
- 65a Gu Y.-Q. Zhang P.-P. Fu J.-K. Liu S. Lan Y. Gong J.-X. Yang Z. Adv. Synth. Catal. 2016; 358: 1392
- 65b Gu Y. Huang J. Gong J. Yang Z. Org. Chem. Front. 2017; 4: 2296
- 66a Aoki S. Watanabe Y. Sanagawa M. Setiawan A. Kotoku N. Kobayashi M. J. Am. Chem. Soc. 2006; 128: 3148
- 66b Aoki S. Watanabe Y. Tanabe D. Arai M. Suna H. Miyamoto K. Tsujibo H. Tsujikawa K. Yamamoto H. Kobayashi M. Bioorg. Med. Chem. 2007; 15: 6758
- 66c Watanabe Y. Aoki S. Tanabe D. Setiawan A. Kobayashi M. Tetrahedron 2007; 63: 4074
- 66d Aoki S. Watanabe Y. Tanabe D. Setiawan A. Arai M. Kobayashi M. Tetrahedron Lett. 2007; 48: 4485
- 67a Nising CF. Brase S. Angew. Chem. Int. Ed. 2008; 47: 9389
- 67b Narayan AR. H. Simmons EM. Sarpong R. Eur. J. Org. Chem. 2010; 3553
- 67c Chen DY. K. Tseng CC. Org. Biomol. Chem. 2010; 8: 2900
- 68a Shenvi RA. Guerrero CA. Shi J. Li CC. Baran PS. J. Am. Chem. Soc. 2008; 130: 7241
- 68b Shi J. Manolikakes G. Yeh CH. Guerrero CA. Shenvi RA. Shigehisa H. Baran PS. J. Am. Chem. Soc. 2011; 133: 8014
- 68c Nicolaou KC. Sun Y.-P. Peng X.-S. Polet D. Chen DY.-K. Angew. Chem. Int. Ed. 2008; 47: 7310
- 68d Nicolaou KC. Peng X.-S. Sun Y.-P. Polet D. Zou B. Lim CS. Chen D. Y.-K. J. Am. Chem. Soc. 2009; 131: 10587
- 68e Lee HM. Nieto-Oberhuber C. Shair MD. J. Am. Chem. Soc. 2008; 130: 16864
- 68f Flyer AN. Si C. Myers AG. Nat. Chem. 2010; 2: 886
- 68g Yamashita S. Iso K. Kitajima K. Himuro M. Hirama M. J. Org. Chem. 2011; 76: 2408
- 68h Nilson MG. Funk RL. J. Am. Chem. Soc. 2011; 133: 12451
- 69a Yamashita S. Iso K. Hirama M. Org. Lett. 2008; 10: 3413
- 69b Yamashita S. Kitajima K. Iso K. Hirama M. Tetrahedron Lett. 2009; 50: 3277
- 69c Simmons EM. Hardin-Narayan AR. Guo X. Sarpong R. Tetrahedron 2010; 66: 4696
- 69d Fang L. Chen Y. Huang J. Liu L. Quan J. Li CC. Yang Z. J. Org. Chem. 2011; 76: 2479
- 69e Kuang LP. Liu LL. Chiu P. Chem. Eur. J. 2015; 21: 14287
- 70a Dai M. Danishefsky SJ. Tetrahedron Lett. 2008; 49: 6610
- 70b Dai M. Wang Z. Danishefsky SJ. Tetrahedron Lett. 2008; 49: 6613
- 70c Kurti L. Czako B. Corey EJ. Org. Lett. 2008; 10: 5247
- 70d Simmons EM. Hardin AR. Guo X. Sarpong R. Angew. Chem. Int. Ed. 2008; 47: 6650
- 70e Kotoku N. Sumii Y. Hayashi T. Kobayashi M. Tetrahedron Lett. 2008; 49: 7078
- 70f Craft DT. Gung BW. Tetrahedron Lett. 2008; 49: 5931
- 70g Magnus P. Littich R. Org. Lett. 2009; 11: 3938
- 70h Yu F. Li G. Gao P. Gong H. Liu Y. Wu Y. Cheng B. Zhai H. Org. Lett. 2010; 12: 5135
- 70i Frie JL. Jeffrey CS. Sorensen EJ. Org. Lett. 2009; 11: 5394
- 70j Baumgartner C. Ma S. Liu Q. Stoltz BM. Org. Biomol. Chem. 2010; 8: 2915
- 70k Liu LL. Chiu P. Chem. Commun. 2011; 3416
- 70l Kotoku N. Sumii Y. Kobayashi M. Org. Lett. 2011; 13: 3514
- 70m Wang Z. Dai MJ. Park PK. Danishefsky SJ. Tetrahedron 2011; 67: 10249
- 70n Aquino C. Greszler SN. Micalizio GC. Org. Lett. 2016; 18: 2624
- 71 Markó IE. Ates A. Gautier A. Leroy B. Plancher J.-M. Quesnel Y. Vanherck J.-C. Angew. Chem. Int. Ed. 1999; 38: 3207
- 72a Huang S.-X. Yang J. Xiao W.-L. Zhu Y.-L. Li R.-T. Li L.-M. Pu J.-X. Li X. Li S.-H. Sun HD. Helv. Chim. Acta 2006; 89: 1169
- 72b Hikino H. Takeshita Y. HiKino Y. Takemoto T. Ito S. Chem. Pharm. Bull. 1967; 15: 485
- 72c Southwell IA. Tucker DJ. J. Essent. Oil Res. 1996; 8: 143
- 72d Peng G.-P. Tian G. Huang X.-F. Lou F.-C. Phytochemistry 2003; 63: 877
- 72e Ratnayake R. Covell D. Ransom TT. Gustafson KR. Beutler JA. Org. Lett. 2009; 11: 57
- 72f Sutthivaiyakit S. Nakorn NN. Kraus W. Sutthivaiyakit P. Tetrahedron 2003; 59: 9991
- 73 Wang LY. Unehara T. Kitanaka S. Chem. Pharm. Bull. 2005; 53: 137
- 74 Dai J. Shi Y. Zhao C. Yang L. J. Chem. Res. 2002; 368
- 75 Bruno M. Rosselli S. Maggio A. Raccuglia RA. Bastow KF. Lee KH. J. Nat. Prod. 2005; 68: 1042
- 76 Jiménez-Núñez E. Molawi K. Echavarren AM. Chem. Commun. 2009; 7327
- 77a Wang C.-L. Sun B.-F. Chen S.-G. Ding R. Lin G.-Q. Xu J.-Y. Shang Y.-J. Synlett 2012; 23: 263
- 77b Wang C.-L. Sun B.-F. Chen S.-G. Ding R. Lin G.-Q. Xu J.-Y. Shang Y.-J. Synlett 2012; 23: 263
- 77c Wang J. Chen S.-G. Sun B.-F. Lin G.-Q. Shang Y.-J. Chem. Eur. J. 2013; 19: 2539
- 78 Zahel M. Wang Y. Jager A. Metz P. Eur. J. Org. Chem. 2016; 5881
- 79 Zhang J. Wang L. Liu Q. Yang Z. Huang Y. Chem. Commun. 2013; 11662
- 80 Dauben WG. Michno DM. J. Org. Chem. 1977; 42: 682
- 81 Rollinger JM. Steindl TM. Schuster D. Kirchmair J. Anrain K. Ellmerer EP. Langer T. Stuppner H. Wutzler P. Schmidtke M. J. Med. Chem. 2008; 51: 842
- 82 Lee J.-H. Choi S. Lee Y. Lee H.-J. Kim K.-H. Ahn K.-S. Bae H. Lee H.-J. Lee E.-O. Ahn K.-S. Ryu SY. Lü J. Kim S.-H. Mol. Cancer Ther. 2010; 9: 389
- 83 Mukaiyama T. Iwasawa N. Chem. Lett. 1981; 29
- 84 Demnitz FW. J. Philippini C. Raphael RA. J. Org. Chem. 1995; 60: 5114
- 85 Tsangarakis C. Arkoudis E. Raptis C. Stratakis M. Org. Lett. 2007; 9: 583
- 86 Yeung YY. Chein RJ. Corey EJ. J. Am. Chem. Soc. 2007; 129: 10346
For a review, see:
For selected examples for synthetic studies, see:
For reviews, see:
For reviews on the synthesis of the cortistatins, see: