Subscribe to RSS
DOI: 10.1055/s-0035-1562623
Vicinal Tricarbonyl Compounds: Versatile Building Blocks for Natural Product Synthesis
Publication History
Received: 12 June 2016
Accepted after revision: 22 July 2016
Publication Date:
22 August 2016 (online)
![](https://www.thieme-connect.de/media/synthesis/201701/lookinside/thumbnails/ss-2016-z0493-sr_10-1055_s-0035-1562623-1.jpg)
Dedicated to Prof. Dieter Enders on the occasion of his 70th birthday
Abstract
Due to their high density of functional groups, vicinal tricarbonyl compounds are versatile building blocks for the synthesis of complex target molecules. Methods for their preparation and their use in stereoselective C–C bond formations, as well as for the synthesis of heteroaromatics, are summarised for the period 2006–2016. Several examples for their applications in natural product synthesis (awajanomycin, cladoniamide, wailupemycin) are presented.
1 Introduction
2 Preparation of Vicinal Tricarbonyl Compounds
3 Use in Stereoselective C–C Bond Formations
4 Use for the Synthesis of Heteroaromatics
5 Examples from Natural Product Synthesis
6 Conclusion
-
References
- 1a Wasserman HH, Parr J. Acc. Chem. Res. 2004; 37: 687
- 1b Wasserman HH. Aldrichimica Acta 1987; 20: 63
- 2 Rubin MB, Gleiter R. Chem. Rev. 2000; 100: 1121
- 3 Kino T, Hatanaka H, Hashimoto M. J. Antibiot. 1987; 40: 1249
- 4 Crown DA. J. Crim. L. Criminology & Police Sci 1969; 60: 258
- 5 Schank K, Blattner R, Bouillon G. Chem. Ber. 1981; 114: 1951
- 6a Sachs F, Harold V. Ber. Dtsch. Chem. Ges. 1907; 40: 2714
- 6b Lombardo LJ, Wasserman HH. Tetrahedron Lett. 1989; 30: 1725
- 7 Regitz M, Adolph HG. Justus Liebigs Ann. Chem. 1969; 723: 47
- 8 Saba A. Synth. Commun. 1994; 24: 695
- 9 Wasserman HH, Han WT. Tetrahedron Lett. 1984; 25: 3743
- 10a Wasserman HH, Vu CB. Tetrahedron Lett. 1990; 31: 5205
- 10b Wasserman HH, Baldino CM, Coats SJ. J. Org. Chem. 1995; 60: 8231
- 12 Dayer F, Dao HL, Gold H, Rode-Gowal H, Dahn H. Helv. Chim. Acta 1974; 57: 2201
- 13 Duschek A, Kirsch SF. Chem. Eur. J. 2009; 15: 10713
- 14 Sivan A, Deepthi A. Tetrahedron Lett. 2014; 55: 1890
- 15a Wang ZL, Li HL, Ge LS, An XL, Zhang ZG, Luo X, Fossey JS, Deng WP. J. Org. Chem. 2014; 79: 1156
- 15b Wang ZL, An XL, Ge LS, Jin JH, Luo X, Deng WP. Tetrahedron 2014; 70: 3788
- 15c Yan J, Ni T, Yan F, Zhang J, Zhuang F. RSC Adv. 2015; 5: 89906
- 16 Sun CQ, Cheng PT. W, Stevensom J, Dejneka T, Brown B, Wang TC, Robl JA, Poss MA. Tetrahedron Lett. 2002; 43: 1161
- 17 Asahara H, Nishiwaki N. J. Org. Chem. 2014; 79: 11735
- 18 Tatsugi J, Izawa Y. J. Chem. Res., Synop. 1988; 356
- 19 Santos MS, Coelho F. RSC Adv. 2012; 2: 3237
- 20 Goswami S, Maity AC, Fun HK, Chantrapromma S. Eur. J. Org. Chem. 2009; 1417
- 21 Yonekawa M, Furusho Y, Sei Y, Takata T, Endo T. Tetrahedron 2013; 69: 4076
- 22 Yuki T, Yonekawa M, Furusho Y, Sei Y, Tomita I, Endo T. Tetrahedron 2016; 72: 2868
- 23 Roßbach J, Baumeister J, Harms K, Koert U. Eur. J. Org. Chem. 2013; 662
- 24 Roßbach J, Harms K, Koert U. Org. Lett. 2015; 17: 3122
- 25 Truong P, Shanahan CS, Doyle MP. Org. Lett. 2012; 14: 3608
- 26 Evans DA, Wu J. J. Am. Chem. Soc. 2005; 127: 8006
- 27 Truong PM, Zavalij PY, Doyle MP. Angew. Chem. Int. Ed. 2014; 53: 6468 ; Angew. Chem. 2014, 126, 6586
- 28 Roßbach J, Harms K, Koert U. Eur. J. Org. Chem. 2014; 993
- 29 Truong P, Xu X, Doyle MP. Tetrahedron Lett. 2011; 52: 2093
- 30 Sha Q, Arman H, Doyle MP. Org. Lett. 2015; 17: 3876
- 31 Truong PM, Mandler MD, Doyle MP. Tetrahedron Lett. 2015; 56: 3042
- 32 Sha Q, Arman H, Doyle MP. Chem. Commun. 2016; 52: 108
- 33 Jang J.-H, Kanoh K, Adachi K, Shizuri Y. J. Nat. Prod. 2006; 69: 1358
- 34a Hiroya K, Kawamoto K, Inamoto K, Sakamoto T, Doi T. Tetrahedron Lett. 2009; 50: 2115
- 34b Pritchard DR, Wilden LD. Tetrahedron Lett. 2010; 51: 1819
- 35a Fu R, Ye JL, Dai XJ, Ruan YP, Huang PQ. J. Org. Chem. 2010; 75: 4230
- 35b Fu R, Chen J, Guo LC, Ye JL, Ruan YP, Huang PQ. Org. Lett. 2009; 11: 5242
- 36a Wohlfahrt M, Harms K, Koert U. Angew. Chem. Int. Ed. 2011; 50: 8404 ; Angew. Chem. 2011, 123, 8554
- 36b Wohlfahrt M, Harms K, Koert U. Angew. Chem. Int. Ed. 2011; 50: 10742 ; Angew. Chem. 2011, 123, 10945
- 36c Wohlfahrt M, Harms K, Koert U. Eur. J. Org. Chem. 2012; 2260
- 37 Williams DE, Davies J, Patrick BO, Bottriell H, Tarling T, Roberge M, Andersen RJ. Org. Lett. 2008; 10: 3501
- 38 Loosley BC, Andersen RJ, Dake GR. Org. Lett. 2013; 15: 1152
- 39 Schütte J, Kilgenstein F, Fischer M, Koert U. Eur. J. Org. Chem. 2014; 5302
- 40 Newman SG, Lautens M. J. Am. Chem. Soc. 2010; 132: 11416
- 41 Kimura T, Kanagaki S, Matsui Y, Imoto M, Watanabe T, Shibasaki M. Org. Lett. 2012; 14: 4418
- 42 Sitachitta N, Gadepalli M, Davidson BS. Tetrahedron 1996; 52: 8073
- 43 Kirsch S, Bach T. Angew. Chem. Int. Ed. 2003; 42: 4685 ; Angew. Chem. 2003, 115, 4833
- 44 Seitz T, Harms K, Koert U. Synthesis 2014; 46: 381
- 45 Schank K, Lieder R, Lick C, Glock R. Helv. Chim. Acta 2004; 87: 869