First total synthesis of (±)-AM6898D and its three diastereoisomers by Claisen rearrangement and stereoselective epimerization

Tetrahedron Letters

Volumn 41, Issue 21, 2000, Pages 4173-4175

  Fukuda, Yoshio ^a   Sakurai, Masahiro ^a   Okamoto, Yasushi ^a  

^a EISAI CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AM6898D; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; IMMUNOGLOBULIN PRODUCTION; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

EID: 0034729303     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00598-0     Document Type: Article

References (9)

1. Yanaginuma, A.; Ishikawa, S. Japanese Patent, 09309859, 1997.
2. (a) For synthesis of (±)-Fumagillin: Corey, E. J.; Snider, B. B. J. Am. Chem. Soc. 1972, 94, 2549-2550.
3. b) For synthesis of (-)-Fumagillin: Taber, D. F.; Christos, T. E.; Rheingold, A. L.; Guzei, I. A. J. Am. Chem. Soc. 1999, 121, 5589-5590.
4. (c) For synthesis of (-)-Fumagillol: Kim, D.; Ahn, S. K.; Bae, H.; Choi, W. J.; Kim, H. S. Tetrahedron Lett. 1997, 38, 4437-4440.
5. Iio, H.; Isobe, M.; Kawai, T.; Goto, T. Tetrahedron 1979, 35, 941-948.
6. 3, 400 MHz) data of 7: [(δ 1.07 ppm, d, J=6.8 Hz, Me-3H), (δ 4.74, 4.84 ppm, brs×2, AB-system, exo-olefin-2H)] and 7′: [(δ 1.16 ppm, d, J=6.8 Hz, Me-3H), (δ 4.65, 4.74 ppm, brs×2, AB-system, exo-olefin-2H)].
7. 3, 400 MHz) data of 8: [(δ 1.11 ppm, d, J=6.8 Hz, Me-3H), (δ 4.77, 4.86 ppm, brs×2, AB-system, exo-olefin-2H)] and 8′: [(δ 1.22 ppm, d, J=6.8 Hz, Me-3H), (δ 4.71, 4.79 ppm, brs×2, AB-system, exo-olefin-2H)].
8. w=0.120, R1=0.061 (2912 reflections), GOF 3.26.
9. Takahashi, T.; Nemoto, H.; Tsuji, J. Tetrahedron Lett. 1983, 24, 3485-3488.