Synthetic studies of 18-membered anti-tumor macrolide, tedanolide. Computer-aided conformational design of a seco-acid derivative for efficient macrolactonization

Tetrahedron Letters

Volumn 37, Issue 3, 1996, Pages 385-388

  Matsushima, Tomohiro ^a   Horita, Kiyoshi ^a   Nakajima, Noriyuki ^a   Yonemitsu, Osamu ^a,b  

^a HOKKAIDO UNIVERSITY   (Japan)

^b OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; MACROLIDE; TEDANOLIDE; UNCLASSIFIED DRUG;

ARTICLE; COMPUTER SIMULATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030024615     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02182-5     Document Type: Article

References (16)

1. Chiral synthesis of polyketide derived natural products, 53. For part 52, see Horita, K.; Tanaka, K.; Inoue, T.; Yonemitsu, O. Tetrahedron, in press.
2. Schmitz, F. J.; Gunasekera, S. P.; Yalamanchili, G. M.; Hossain, B; van der Helm, P. J. Am. Chem. Soc. 1984, 106, 7251.
3. Hikota, M.; Tone, H.; Horita, K.; Yonemitsu, O. J. Org. Chem. 1990, 55, 9; Tetrahedron 1990, 46, 4613.
4. Hikota, M.; Tone, H.; Horita, K.; Yonemitsu, O. J. Org. Chem. 1990, 55, 9; Tetrahedron 1990, 46, 4613.
5. a) Nakajima, N.; Uoto, K.; Matsushima, T.; Yomemitsu, O.; Goto, H.; Osawa, E. J. Org. Chem. 1990, 55, 1129.
6. b) Nakajima, N.; Matsushima, T.; Yomemitsu, O.; Goto, H.; Osawa, E. Chem. Pharm. Bull. 1991, 39, 64.
7. Stork, G.; Rychnovsky, S. D. J. Am. Chem. Soc. 1987, 109, 1565.
8. The S-hydroxy groups are directed toward the outside of the lactone ring, and are favorable for the oxidation into the carbonyl groups.
9. Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1992, 31, 1124.
10. a) Goto, H.; Osawa, E. Tetrahedron Lett. 1992, 33, 1343.
11. b) Goto, H.; Osawa, E. J. Chem. Soc., Perkin Trans. 2 1993, 187.
12. c) Goto, H.; Osawa, E.; Yamato, M. Tetrahedron 1993, 49, 387.
13. Most of the containers (85%) are in this global conformation except for the side-chain rotation.
14. Details for the synthesis of 2 and 3 will be reported soon.
15. Inanaga, J.; Hirata, K.; Saeki, T.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989.
16. The methyl ester was synthesized by treatment of the mixed anhydride of 3 with methanol.