Synthesis of (4R,15R,16R,21S)- and (4R,15S,16S,21S)-rollicosin

Tetrahedron Letters

Volumn 46, Issue 27, 2005, Pages 4671-4675

  Makabe, Hidefumi ^a   Higuchi, Masaharu ^a   Konno, Hiroyuki ^b   Murai, Masatoshi ^c   Miyoshi, Hideto ^c  

^a SHINSHU UNIVERSITY   (Japan)

^b KYOTO PREFECTURAL UNIVERSITY OF MEDICINE   (Japan)

^c KYOTO UNIVERSITY   (Japan)

Author keywords

Annonaceous acetogenin; Antitumor; Mitochondrial complex I

Indexed keywords

4 PENTYN 1 OL; 5 HEXEN 1 OL; ALCOHOL DERIVATIVE; GAMMA LACTONE DERIVATIVE; LACTONE DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE DEHYDROGENASE (UBIQUINONE); ROLLICOSIN; UNCLASSIFIED DRUG;

ARTICLE; COW; DRUG ACTIVITY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HEART MITOCHONDRION;

BOVINAE;

EID: 20344402043     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.04.144     Document Type: Article

References (24)

1. For recent reviews for Annonaceous acetogenins, see: F.Q. Alali, X.-X. Liu, and J.L. McLaughlin J. Nat. Prod. 62 1999 504 540
2. M.C. Zafra-Polo, B. Figadère, T. Gallardo, J.R. Tormo, and D. Cortes Phytochemistry 48 1998 1087 1117
3. C.-C. Liaw, F.-R. Chang, M.-J. Wu, and Y.-C. Wu J. Nat. Prod. 66 2003 279 281
4. S.H. Myint, A. Laurens, R. Hocquemiller, A. Cavé, D. Davoust, and D. Cortes Heterocycles 31 1990 861 867
5. M.H. Woo, Q. Ye, Z.-M. Gu, G.-X. Zhao, and J.L. McLaughlin Bioorg. Med. Chem. Lett. 5 1995 1135 1140
6. For isolation: M.J. Rieser, J.F. Kozlowski, K.V. Wood, and J.L. McLaughlin Tetrahedron Lett. 32 1991 1137 1140
7. For synthesis: E. Keinan, S. Sinha, S.B. Anjana, Z.M. Wang, X.L. Zhang, and K.B. Sharpless Tetrahedron Lett. 33 1992 6307 6410
8. H. Makabe, A. Tanaka, and T. Oritani Biosci. Biotechnol. Biochem. 57 1993 1028 1029
9. J.-L. Lee, C.-F. Lin, L.-Y. Hsieh, H.-F. Chiu, Y.-C. Wu, K.-S. Wang, and M.-J. Wu Tetrahedron Lett. 44 2003 7833 7835
10. J.D. White, T.C. Somers, and G.N. Reddy J. Org. Chem. 57 1992 4991 4998
11. K.B. Sharpless, W. Amberg, Y.L. Bennani, G.A. Crispino, J. Hartung, K.-S. Jeong, H.-L. Kwong, K. Morikawa, Z.-M. Wang, D. Xu, and X.-L. Zhang J. Org. Chem. 57 1992 2768 2771
12. H. Becker, and K.B. Sharpless Angew. Chem., Int. Ed. 35 1996 448 451
13. W.-Q. Yang, and T. Kitahara Tetrahedron Lett. 40 1999 7827 7830
14. K. Sonogashira, Y. Tohda, and N. Hagihara Tetrahedron Lett. 16 1975 4467 4470
15. H. Makabe, A. Miyawaki, R. Takahashi, Y. Hattori, H. Konno, M. Abe, and H. Miyoshi Tetrahedron Lett. 45 2004 973 977
16. 6: 397.2592. Found 397.2601
17. 13C NMR of 1 synthesized by us matched very well with those by K. J. Quinn and co-workers
18. The discrepancy in the optical rotation value of the synthetic product with that reported for the natural product has been reported.: S.C. Sinha, S.C. Sinha, and E. Keinan J. Org. Chem. 64 1999 7067 7073
19. S. Takahashi, A. Kubota, and T. Nakata Org. Lett. 5 2003 1353 1356
20. Ref. 12
21. 4Si) δ: 19.12, 21.17, 25.41, 25.55, 28.70, 29.41, 29.47, 31.98, 33.41, 33.46, 37.43, 69.99, 71.49, 77.98, 82.82, 131.23, 151.81, 174.59, 177.38
22. 6: 397.2592. Found 397.2586
23. H. Miyoshi, M. Ohshima, H. Shimada, T. Akagi, H. Iwamura, and J.L. McLaughlin Biochim. Biophys. Acta 1365 1998 443 452
24. T. Motoyama, H. Yabunaka, and H. Miyoshi Bioorg. Med. Chem. Lett. 12 2002 2089 2092