Enantioselective synthesis of 15-epi-haterumalide NA methyl ester and revised structure of haterumalide NA

Organic Letters

Volumn 5, Issue 6, 2003, Pages 957-960

  Kigoshi, Hideo ^a,b   Kita, Masaki ^a,b   Ogawa, Seiji ^a,b   Itoh, Masahiro ^a,b   Uemura, Daisuke ^a,b  

^a UNIVERSITY OF TSUKUBA   (Japan)

^b NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

15 EPIHATERUMALIDE NA METHYL ESTER; ALKENE DERIVATIVE; CYTOTOXIC AGENT; HATERUMALIDE NA; MACROLIDE; THREITOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; DERIVATIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; REFORMATSKY REACTION; SPONGE (PORIFERA); STEREOCHEMISTRY;

EID: 0141739284     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0341804     Document Type: Article

References (27)

1. Takada, N.; Sato, H.; Suenaga, K.; Arimoto, H.; Yamada, K.; Ueda, K.; Uemura, D. Tetrahedron Lett. 1999, 40, 6309.
2. Ueda, K.; Hu, Y. Tetrahedron Lett. 1999, 40, 6305.
3. Strobel, G.; Li, J.-Y.; Sugawara, F.; Koshino, H.; Harper, J.; Hess, W. M. Microbiology 1999, 145, 3557.
4. Thaning, C.; Welch, C. J.; Borowicz, J. J.; Hedman, R.; Gerhardson, B. Soil Biol. Biochem. 2001, 33, 1817.
5. 2 and (2) Jones oxidation.
6. Yadav, J. S.; Deshpande, P. K.; Sharma, G. V. M. Tetrahedron 1990, 46, 7033.
7. Ogura, K.; Tsuchihashi, G. Tetrahedron Lett. 1971, 34, 3151.
8. Dondoni, A.; Fantin, G.; Foganolo, M.; Merino, P. Tetrahedron Lett. 1990, 31, 4513.
9. 1H NMR data and the NOE experiments.
10. (a) Miller, R. B.; Al-Hassan, M. I. J. Org. Chem. 1983, 48, 4113.
11. (b) Zweifel, G.; Lewis, W. J. Org. Chem. 1978, 43, 2739.
12. Tamao, K.; Akita, M.; Maeda, K.; Kumada, M. J. Org. Chem. 1987, 52, 1100.
13. Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405.
14. (a) Corey, E. J.; Weigel, L. O.; Chamberlin, R.; Cho, H.; Hua, D. H. J. Am. Chem. Soc. 1980, 102, 6613.
15. (b) Mioskowski, C.; Solladie, G. Tetrahedron 1980, 36, 227.
16. (c) Solladie, G.; Moghadam, F.-M. J. Org. Chem. 1982, 47, 91.
17. Mioskowski, C.; Solladie, G. Tetrahedron Lett. 1975, 3341.
18. Diastereoselectivity of this aldol reaction was 95:5, and the mixture could be chromatographically separated.
19. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
20. (a) Tabuchi, T.; Kawamura, K.; Inagawa, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 3889.
21. (b) Molander, G. A.; Etter, J. B.; Harring, L. S.; Thorel, P.-J. J. Am. Chem. Soc. 1991, 113, 8036.
22. The calculations were executed by MacroModel (Version 6.0) with the MM2* force field.
23. Rathke, M. W.; Lindert, A. J. Org. Chem. 1970, 35, 3966.
24. Maruoka, K.; Hashimoto, S.; Kitagawa, Y.; Yamamoto, H.; Nozaki, H. Bull. Chem. Soc. Jpn. 1980, 53, 3301.
25. Kanai, K.; Wakabayashi, H.; Honda, T. Org. Lett. 2000, 2, 2549.
26. The stereochemistry at the C-4 double bond was easily determined by the NOE experiments. On the other hand, the stereochemistry at C-3 was determined by the modified Mosher's method. The minor isomer, (3S,4Z)-35, could not be transformed into the corresponding MTPA esters because of the instability during the methanolysis of the acetyl group. However, the modified Mosher's method could be applied to (3R,4Z)-37 that was obtained by methanolysis of the major isomer, (3R,4Z)-35, establishing that the major isomer possessed the undesired stereochemistry 3R, i.e., the minor isomer was the desired (3S)-compound.
27. Takai, K.; Tagashira, M.; Kuroda, T.; Oshima, K.; Utimoto, K.; Nozaki, H. J. Am. Chem. Soc. 1986, 108, 6048.