Total synthesis of (-)-samaderine Y from (S)-(+)-carvone

Angewandte Chemie - International Edition

Volumn 44, Issue 48, 2005, Pages 7981-7984

  Shing, Tony K M ^a   Yeung, Ying Y ^a  

^a CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

Antitumor agents; Fused ring systems; Natural products; Quassinoids; Total synthesis

Indexed keywords

CYTOLOGY; TOXICITY; TUMORS;

ANTITUMOR AGENTS; FUSED-RING SYSTEMS; NATURAL PRODUCTS; QUASSINOIDS; TOTAL SYNTHESIS;

SYNTHESIS (CHEMICAL);

ANTINEOPLASTIC AGENT; CARVONE; QUASSINOID DERIVATIVE; SAMADERINE Y; TERPENE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ANTINEOPLASTIC AGENTS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; MOLECULAR STRUCTURE; MONOTERPENES; QUASSINS; STEREOISOMERISM;

EID: 29144498430     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200502763     Document Type: Article

References (23)

1. For a recent review, see: Z. Guo, S. Vangapandu, R. W. Sindelar, L. A. Walker, R. D. Sindelar, Curr. Med. Chem. 2005, 12, 173-190.
2. For some reports of total syntheses of pentacyclic quassinoids, see: a) (dl)-samaderine B: P. A. Grieco, M. M. Piñeiro-Nuñez, J. Am. Chem. Soc. 1994, 116, 7606-7615;
3. b) (-)-chaparrinone, (-)-glaucarubolone, and (+)-glaucarubinone: P. A. Grieco, J. L. Collins, E. D. Moher, T. J. Fleck, R. S. Gross, J. Am. Chem. Soc. 1993, 115, 6078-6093;
4. c) simalikalactone D: E. D. Moher, J. L. Collins, P. A. Grieco, J. Am. Chem. Soc. 1992, 114, 2764-2765.
5. a) I. Kitagawa, T. Mahmud, K. Yokota, S. Nakagawa, T. Mayumi, M. Kobayashi, H. Shibuya, Chem. Pharm. Bull. 1996, 44, 2009-2014;
6. b) H. Aono, K. Koike, J. Kaneko, T. Ohmoto, Phytochemistry 1994, 37, 579-584.
7. a) T. K. M. Shing, X. Y. Zhu, Y. Y. Yeung, Chem. Eur. J. 2003, 9, 5489-5500;
8. b) T. K. M. Shing, Q. Jiang, Tetrahedron Lett. 2001, 42, 5271-5273.
9. W. G. Salmond, M. A. Barta, J. L. Havens, J. Org. Chem. 1978, 43, 2057-2059.
10. J. L. Luche, L. Rodriguez-Hahn, P. Crabbe, J. Chem. Soc. Chem. Commun. 1978, 14, 601-602.
11. CCDC 235459 (7) and 266924 (29) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data_request/cif.
12. S. V. Ley, J. Norman, W. P. Griffith, S. P. Marsden, Synthesis 1994, 7, 639-666.
13. S. R. Wilson, D. T. Mao, K. M. Jernberg, S. T. Ezmirly, Tetrahedron Lett. 1977, 18, 2559-2562.
14. K. Shishido, T. Omodani, M. Shibuya, J. Chem. Soc. Perkin Trans. 1 1991, 9, 2285-2287.
15. T. K. M. Shing, V. E. F. Tai, J. Org. Chem. 1995, 60, 5332-5334.
16. T. K. M. Shing, Y. Tang, J. Chem. Soc. Perkin Trans. 1 1994, 12, 1625-1631.
17. J. Muzart, Chem. Rev. 1992, 92, 113-140.
18. T. K. M. Shing, Y. Y. Yeung, P. L. So, unpublished results.
19. R. C. Cambie, M. P. Hay, L. Larsen, C. E. F. Rickard, P. S. Rutledge, P. D. Woodgate, Aust. J. Chem. 1991, 44, 821-842.
20. D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 1991, 113, 7277-7287.
21. a) M. Fetizon, M. Golfier, C. R. Acad. Sci. Ser. C 1968, 267, 900-903;
22. b) M. Fetizon, M. Golfier, J. M. Louis, J. Chem. Soc. D 1969, 19, 1102;
23. c) M. Fetizon, M. Golfier, P. Mourgues, Tetrahedron Lett. 1972, 13, 4445-4448.