Total synthesis and stereochemical confirmation of manassantin A, B, and B1

Organic Letters

Volumn 8, Issue 24, 2006, Pages 5477-5480

  Hanessian, Stephen ^a   Reddy, Gone Jayapal ^a   Chahal, Navjot ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL ALCOHOL DERIVATIVE; CYANOHYDRIN; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FURAN DERIVATIVE; HYPOXIA INDUCIBLE FACTOR 1; MANASSANTIN A; MANASSANTIN B; NEUROLEPTIC AGENT; NITRILE; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; DRUG ANTAGONISM; METHYLATION; SAURURACEAE; STEREOISOMERISM; SYNTHESIS;

ANTIPSYCHOTIC AGENTS; BENZYL ALCOHOLS; FURANS; HYPOXIA-INDUCIBLE FACTOR 1; INDICATORS AND REAGENTS; METHYLATION; NITRILES; SAURURACEAE; STEREOISOMERISM; TUMOR NECROSIS FACTOR-ALPHA;

EID: 33846009806     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0621710     Document Type: Article

References (35)

1. (a) Rao, K. V.; Alvarez, F. M. Tetrahedron Lett. 1983, 24, 4947.
2. (b) Rao, K. V.; Oruganty, R. S. J. Liq. Chromatogr. Rel. Technol. 1997, 20, 3121.
3. (c) Hodges, T. W.; Hossain, C. F.; Kim, Y.-P.; Zhou, Y.-D.; Nagle, D. G. J. Nat. Prod. 2004, 67, 767.
4. (d) Hossain, C. F.; Kim, Y.-P.; Baerson, S. R.; Zhang, L.; Bruick, R. K.; Mohammed, K. A.; Agarwal, A. K.; Nagle, D. G.; Zhou, Y.-D. Biochem. Biophys. Res. Commun. 2005, 333, 1026.
5. (a) Hwang, B. Y.; Lee, J.-H.; Nam, J. B.; Hong, Y.-S.; Lee, J. J. Phytochemistry 2003, 64, 765.
6. (b) Lee, W. S.; Lee, D.-W.; Baek, Y.-I.; An, S.-J.; Cho, K.-H.; Choi, Y.-K.; Kim, H.-C.; Park, H. Y.; Bae, K.-H.; Jeong, T.-S. Bioorg. Med. Chem. Lett. 2004, 14, 3109.
7. (a) Hartwell, J. L. Lloydia 1971, 34, 204.
8. (b) Phares, D. L. Am. J. Pharm. 1987, 39, 468.
9. (c) Chung, B. S.; Shin, M. G. Dictionary of Korean Folk Medicine; Young Lim sa: Seoul, 1990; p 813.
10. (a) Semenza, G. L. Nat. Rev. Cancer 2003, 3, 721.
11. (b) Clottes, E. Bull. Cancer 2005, 92, 119.
12. (c) Moeller, B. J.; Dewhirst, M. W. Br. J. Cancer 2006, 95, 1.
13. Song, S.-Y.; Lee, I.; Park, C.; Lee, H.; Hahm, J.-C.; Kang, W. K. Int. J. Mol. Med. 2005, 16, 517.
14. Hahm, J.-C.; Lee, I.-K.; Kang, W.-K.; Kim, S.-U.; Ahn, Y.-J. Planta Med. 2005, 71, 464.
15. Kwon, O. E.; Lee, H. S.; Lee, S. W.; Chung, M. Y.; Bae, K. H.; Rho, M.-C.; Kim, Y.-K. Arch. Pharm. Res. 2005, 28, 55.
16. Rao, K. V.; Puri, V. N.; Sawaf, H. A. E. Eur. J. Pharmacol. 1990, 179, 367.
17. Belokon, Y. N.; North, M.; Parsons, T. Org. Lett. 2000, 2, 1617.
18. (a) Hanessian, S.; Sumi, K. Synthesis 1991, 1083.
19. (b) Hanessian, S.; Gai, Y.; Wang, W. Tetrahedron Lett. 1996, 37, 7473.
20. (c) Hanessian, S.; Wang, W.; Gai, Y. Tetrahedron Lett. 1996, 37, 7477.
21. See Supporting Information (Table 1).
22. Imamoto, T.; Takiyama, N.; Nakamura, K.; Hatajima, T.; Kamiya, Y. J. Am. Chem. Soc. 1989, 111, 4392.
23. Schwesinger, R.; Schlemper, H. Angew. Chem., Int. Ed. Engl. 1987, 26, 1167.
24. Shimizu, T.; Osako, K.; Nakata, T. Tetrahedron Lett. 1997, 38, 2685.
25. See also: Basha, A.; Lipton, M.; Weinreb, S. M. Tetrahedron Lett. 1977, 18, 4171.
26. Lee, A.-L.; Ley, S. V. Org. Biomol. Chem. 2003, 1, 3957.
27. Biftu, T.; Gamble, N. F.; Doebber, T.; Hwang, S.-B.; Shen, T.-Y.; Snyder, J.; Springer, J. P.; Stevenson, R. J. Med. Chem. 1986, 29, 1917.
28. Yamauchi, S.; Okazaki, M.; Akiyama, K.; Sugahara, T.; Kishida, T.; Kashiwagi, T. Org. Biomol. Chem. 2005, 3, 1670.
29. (a) Moinuddin, S. G. A.; Hishiyama, S.; Cho, M.-H.; Davin, L. B.; Lewis, N. G. Org. Biomol. Chem. 2003, 1, 2307.
30. (b) Stevenson, R.; Williams, J. R. Tetrahedron 1977, 33, 285.
31. Esumi, T.; Hojyo, D.; Zhai, H.; Fukuyama, Y. Tetrahedron Lett. 2006, 47, 3979.
32. (a) Coleman, R. S.; Gurrala, S. R. Org. Lett. 2004, 6, 4025.
33. (b) Yu, S. H.; Ferguson, M. J.; McDonald, R.; Hall, D. G. J. Am. Chem. Soc. 2005, 127, 12808.
34. The minor isomer 13b had resulted from a face-selective attack of the distal benzylic alcohol via a quinonoid oxocarbenium ion with ejection of the OMOM group to giva an anti-anti-anti pattern. See Supporting Information (Scheme 1).
35. Otera, J.; Nakazawa, K.; Sekoguchi, K.; Orita, A. Tetrahedron 1997, 53, 13633.