Synthesis of Amaryllidaceae Constituents - An Update

Uwe Rinner; Tomas Hudlicky

doi:10.1055/s-2005-862382

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Synlett 2005(3): 365-387
DOI: 10.1055/s-2005-862382

ACCOUNT

Synthesis of Amaryllidaceae Constituents - An Update

Uwe Rinner^b, Tomas Hudlicky*^a
^a Department of Chemistry, Brock University, 500 Glenridge Avenue, St. Catharines, Ontario L2S 3A1, Canada
Fax: +1(905)9844841; e-Mail: thudlicky@brocku.ca;
^b Institut für Organische Chemie, Universität Wien, Währinger Strasse 38, 1090 Wien, Austria
Fax: +43(0)1427752189; e-Mail: uwe.rinner@univie.ac.at;

Further Information

Publication History

Received 15 June 2004
Publication Date:
04 February 2005 (online)

Abstract
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Abstract

Recent progress in the synthesis of major constituents of the Amaryllidaceae family is reviewed. Total syntheses of pancratistatin, narciclasine, and their 7-deoxy- derivatives, 7-deoxypancratistatin and lycoricidine, respectively, are covered in detail. Also included are preparations of truncated derivatives and unnatural mimics of pancratistatin. The literature coverage begins with the publication of the last major review in 1996 and is complete through the fall of 2004.

1 Introduction
2 Total Syntheses
2.1 Pancratistatin
2.1.1 Haseltine (1997)
2.1.2 Magnus (1998)
2.1.3 Rigby (2000)
2.1.4 Pettit (2001)
2.1.5 Kim (2002)
2.2 7-Deoxypancratistatin
2.2.1 Keck (1998)
2.2.2 Plumet (2000)
2.3 Narciclasine
2.3.1 Rigby (1997)
2.3.2 Hudlicky (1999)
2.3.3 Keck (1999)
2.3.4 Yan (2002)
2.4 Lycoricidine
2.4.1 Keck (1999)
2.4.2 Yan (2002)
3 Unnatural and Truncated Derivatives
3.1 ent-Lycoricidine (Keck, 1996)
3.2 ent-7-Deoxypancratistatin (Hudlicky, 1999)
3.3 Positional Isomer of 7-Deoxypancratistatin (Hudlicky, 2000)
3.4 epi-7-Deoxypancratistatin (Hudlicky, 2001)
3.5 Deoxygenated Derivative of 7-Deoxypancratistatin
(McNulty, 2001)
3.6 Truncated Derivative of 7-Deoxypancratistatin (Hudlicky, 2002)
3.7 Deoxygenated Derivative of 7-Deoxypancratistatin (Hudlicky, 2004)
3.8 Carbohydrate Analog of 7-Deoxypancratistatin (Fessner, 2004)
3.9 β-Carboline-1-one Analog of Pancratistatin (Hudlicky, 2004)
4 Conclusion

Key words

total synthesis - Amaryllidaceae constituents (alkaloids) - unnatural and truncated derivatives

References

2 Hartwell JL. Lloydia 1967, 30: 379

Google Scholar
3 Fitzgerald R. Hartwell JL. Leiter J. J. Nat. Cancer Inst. 1958, 20: 763

Google Scholar
4 Carrasco L. Fresno M. Vazquez D. FEBS Lett. 1975, 52: 236

Crossref Google Scholar
5 Jimenez A. Sanchez L. Vazquez D. FEBS Lett. 1975, 55: 53

Crossref Google Scholar
6 Mondon A. Krohn K. Chem. Ber. 1975, 108: 445

Crossref Google Scholar
7 Baez A. Vazquez D. Biochim. Biophys. Acta 1978, 518: 95

Crossref Google Scholar
8 Rivera G. Gosalbez M. Ballesta JPG. Biochem. Biophys. Res. Commun. 1980, 94: 800

Crossref Google Scholar
9 Pettit GR. Gaddamidi V. Cragg GM. Herald DL. Sagawa Y. J. Chem. Soc., Chem. Commun. 1984, 1693

Crossref Google Scholar
10 Pettit GR. Freeman S. Simpson MJ. Thompson MA. Boyd MR. Williams GR. Pettit GR. Doubek DL. Anti-Cancer Drug Des. 1995, 10: 243

Google Scholar
11 Pettit GR. Orr S. Ducki S. Anti-Cancer Drug Des. 2000, 15: 389

Google Scholar
12 Pettit GR. Gaddamidi V. Herald DL. Singh SB. Cragg GM. Schmidt JM. Boettner FE. Williams M. Sagawa Y. J. Nat. Prod. 1986, 49: 995

Crossref Google Scholar
13 Tsuda Y. Sano T. Tag JI. Isobe K. Toda J. Takagi S. Yamaki M. Murata M. Irie H. Tanaka H. J. Chem. Soc., Perkin Trans. 1 1979, 1358

Crossref Google Scholar
14 Danishefsky S. Lee JY. J. Am. Chem. Soc. 1989, 111: 4829

Crossref Google Scholar
15 Tian XR. Hudlicky T. Königsberger K. J. Am. Chem. Soc. 1995, 117: 3643

Crossref Google Scholar
For reviews see:
16a Martin SF. In The Alkaloids Vol. 40: Brossi AR. Academic; New York: 1987. p.251

Crossref PubMed Google Scholar
16b Polt R. In Organic Synthesis: Theory and Applications Vol 3: Hudlicky T. JAI Press; Greenwich, CT: 1997. p.109

Crossref PubMed Google Scholar
16c Hoshino O. In The Alkaloids Vol 51: Cordell GA. Academic; New York: 1998. p.323

Crossref PubMed Google Scholar
16d Jin Z. Nat. Prod. Rep. 2003, 20: 606

Crossref PubMed Google Scholar
17 Ohta S. Kimoto S. Tetrahedron Lett. 1975, 2279

Crossref Google Scholar
18 Paulsen H. Stube M. Tetrahedron Lett. 1982, 23: 3171

Crossref Google Scholar
19 Paulsen H. Stubbe M. Liebigs Ann. Chem. 1983, 535

Google Scholar
20 Ugarkar BG. DaRe J. Schubert EM. Synthesis 1987, 715

Article in Thieme Connect Google Scholar
21 Chida N. Ohtsuka M. Ogawa S. Tetrahedron Lett. 1991, 32: 4525

Crossref Google Scholar
22 Hudlicky T. Olivo HF. J. Am. Chem. Soc. 1992, 114: 9694

Crossref PubMed Google Scholar
23 Trost BM. Pulley SR. J. Am. Chem. Soc. 1995, 117: 10143

Google Scholar
24 Tian X. Maurya R. Königsberger K. Hudlicky T. Synlett 1995, 1125

Article in Thieme Connect Google Scholar
25 Keck GE. McHardy SF. Murry JA. J. Am. Chem. Soc. 1995, 117: 7289

Crossref Google Scholar
26 Chida N. Jitsuoka M. Yamamoto Y. Ohtsuka M. Ogawa S. Heterocycles 1996, 53: 1385

Google Scholar
27 Hudlicky T. Tian X. Königsberger K. Maurya R. Rouden J. Fan B. J. Am. Chem. Soc. 1996, 118: 10752

Crossref Google Scholar
28 Doyle TJ. Hendrix M. VanDerveer D. Javanmard S. Haseltine J. Tetrahedron 1997, 53: 11153

Crossref Google Scholar
29 Rigby JH. Mateo ME. J. Am. Chem. Soc. 1997, 119: 12655

Crossref Google Scholar
30 Magnus P. Sebhat IK. J. Am. Chem. Soc. 1998, 120: 5341

Crossref Google Scholar
31 Keck GE. Wager TT. McHardy SF. J. Org. Chem. 1998, 63: 9164

Crossref Google Scholar
32 Gonzalez D. Martinot T. Hudlicky T. Tetrahedron Lett. 1999, 40: 3077

Crossref Google Scholar
33 Keck GE. Wager TT. Rodriquez FD. J. Am. Chem. Soc. 1999, 121: 5176

Crossref Google Scholar
34 Rigby JH. Maharoof USM. Mateo ME. J. Am. Chem. Soc. 2000, 122: 6624

Crossref Google Scholar
35 Acena JL. Arjona O. Leon ML. Plumet J. Org. Lett. 2000, 2: 3683

Crossref Google Scholar
36 Pettit GR. Melody N. Herald DL. J. Org. Chem. 2001, 66: 2583

Crossref Google Scholar
37 Kim S. Ko H. Kim E. Kim D. Org. Lett. 2002, 4: 1343

Crossref Google Scholar
38 Elango S. Yan T.-H. J. Org. Chem. 2002, 67: 6954

Crossref Google Scholar
39 Elango S. Yan T.-H. Tetrahedron 2002, 58: 7335

Crossref Google Scholar
40 Knapp S. Ornaf RM. Rodriques KE. J. Am. Chem. Soc. 1983, 105: 5494

Crossref Google Scholar
41 Magnus P. Lacour J. Evans PA. Roe MB. Hulme C. J. Am. Chem. Soc. 1996, 118: 3406

Crossref Google Scholar
42 Banwell MG. Cowden CJ. Gable RW. J. Chem. Soc., Perkin Trans. 1 1994, 3515

Crossref Google Scholar
43 McGowen DA. Berchtold GA. J. Org. Chem. 1981, 46: 2381

Google Scholar
44 Hoare JH. Policastro PP. Berchtold GA. J. Am. Chem. Soc. 1983, 105: 6264

Crossref Google Scholar
45 Pawlak JL. Berchtold GA. J. Org. Chem. 1987, 52: 1765

Google Scholar
46 Piozzi F. Fugante C. Mondelli R. Ceriotti G. Tetrahedron 1968, 24: 1119

Crossref Google Scholar
47 Pettit GR. Sing SB. Can. J. Chem. 1987, 65: 2390

Crossref Google Scholar
48 Kim S. Cheong JH. Yoon KS. Tetrahedron Lett. 1995, 36: 6096

Google Scholar
49 Kim S. Kee IS. Lee S. J. Am. Chem. Soc. 1991, 113: 9882

Crossref Google Scholar
50 Fleet GWJ. Ramsden NG. Witty DR. Tetrahedron 1989, 45: 319

Crossref Google Scholar
51 Arjona O. Iradier F. Plumet J. Martnez-Alcazar MP. Hernandez-Cano F. Fonseca I. Tetrahedron Lett. 1998, 39: 6741

Crossref Google Scholar
52 Gibson DT. Hensley M. Yoshioka H. Mabry TJ. Biochemistry 1970, 9: 1626

Crossref Google Scholar
53 Zylstra GJ. Gibson DT. J. Biol. Chem. 1989, 264: 14940

Google Scholar
54 Keck GE. Wager TT. J. Org. Chem. 1996, 61: 8366

Crossref Google Scholar
55 Gilman NW. J. Chem. Soc., Chem. Commun. 1971, 733

Google Scholar
56 Fleet GWJ. Ramsden NG. Witty DR. Tetrahedron 1989, 45: 319

Crossref Google Scholar
57 Rinner U. Siengalwicz P. Hudlicky T. Org. Lett. 2001, 4: 115

Google Scholar
58 Keck GE. Fleming S. Nickell D. Weider P. Synth. Commun. 1979, 9: 281

Crossref Google Scholar
59 Keck GE. Kachensky DF. Enholm EJ. J. Org. Chem. 1985, 50: 4317

Google Scholar
60 Akgün H. Hudlicky T. Tetrahedron Lett. 1999, 40: 3081

Crossref Google Scholar
61 Allen CCR. Boyd DR. Dalton H. Sharma ND. Brannigan I. Kerley NA. Sheldrake GN. Taylor SC. J. Chem. Soc., Chem. Commun. 1995, 117

Crossref Google Scholar
62 Hudlicky T. Olivo HF. McKibben B. J. Am. Chem. Soc. 1994, 116: 5108

Crossref Google Scholar
63 Johnson CR. Adams JP. Collins MA. J. Chem. Soc., Perkin Trans. 1 1993, 1

Crossref Google Scholar
64 Olivo HF. Hemenway MS. Hartwig AC. Chan R. Synlett 1998, 247

Article in Thieme Connect Google Scholar
65 Schilling S. Rinner U. Chan C. Ghiviriga I. Can. J. Chem. 2001, 79: 1659

Crossref Google Scholar
66 Gibson DT. Koch JR. Shuld CL. Kallio RE. Biochemistry 1968, 7: 3795

Crossref Google Scholar
67 Hudlicky T. Stabile MR. Gibson DT. Whited GM. Org. Synth. 1999, 76: 77

Google Scholar
68 Yamada Y. Yamamoto T. Okawara M. Chem. Lett. 1975, 361

Crossref Google Scholar
69 Evans DA. Faul MM. Biledou MT. J. Org. Chem. 1991, 56: 6744

Crossref PubMed Google Scholar
70 Li Z. Conser KR. Jacobsen EN. J. Am. Chem. Soc. 1993, 115: 5326

Google Scholar
71 Kim BM. Sharpless KB. Tetrahedron Lett. 1989, 30: 655

Crossref Google Scholar
72 McNulty J. Mao J. Gibe R. Mo R. Wolf S. Pettit GR. Herald DL. Boyd MR. Bioorg. Med. Chem. Lett. 2001, 11: 169

Crossref Google Scholar
73 Hudlicky T. Rinner U. Gonzalez D. Akgun H. Schilling S. Siengalewicz P. Martinot TA. Pettit GR. J. Org. Chem. 2002, 67: 8726

Crossref Google Scholar
74 Rinner U. Hillebrenner H. Adams DR. Hudlicky T. Pettit GR. Bioorg. Med. Chem. Lett. 2004, 14: 2911

Crossref Google Scholar
75 Mandel M. Hudlicky T. Kwart LD. Whited GM. J. Org. Chem. 1993, 58: 2331

Google Scholar
76 Phung AN. Zannetti MT. Whited G. Fessner W.-D. Angew. Chem. Int. Ed. 2003, 42: 4821

Crossref Google Scholar
77 Ibn-Ahmed S. Khaldi M. Chretien K. Chapleur Y. J. Org. Chem. 2004, 69: 6722 ; this article appeared after the final version of our review was submitted and thus the details of the chemistry were not included

Crossref Google Scholar
78 Rinner U. Hudlicky T. Gordon H. Pettit GR. Angew. Chem. Int. Ed. 2004, 43: 5342

Crossref Google Scholar
79 Pettit GR. Melody N. Herald DL. Schmidt JM. Pettit RK. Chapuis J.-C. Heterocycles 2002, 56: 139

Crossref Google Scholar

1

The pancratistatin, narciclasine, and lycoricidine group of natural products has collectively been referred to as ‘Amaryllidaceae alkaloids’ by most, if not all, synthetic chemists (Martin, Hudlicky, Keck, Polt, and others). Such nomenclature is not accurate, as these compounds do not contain basic nitrogen atoms. Another term used in the literature is ‘isocarbostyril’ (Pettit), a term which is not generally known in the synthetic community. To avoid further inaccuracies we will avoid both names in future publications and simply refer to these compounds as ‘constituents’.