Synthetic study on azadirachtin (Part 2). Construction of the decalin moiety with full functionality on B-ring

Tetrahedron Letters

Volumn 38, Issue 25, 1997, Pages 4429-4432

  Watanabe, Hidenori ^a   Watanabe, Takeru ^a   Mori, Kenji ^b   Kitahara, Takeshi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AZADIRACHTIN;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

BETULACEAE; INSECTA;

EID: 0030912457     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00923-4     Document Type: Article

References (16)

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2. Reviews: a) Ley, S. V; Denholm, A. A.; Wood, A. Nat. Prod. Rep. 1993, 109-157.
3. b) Mordue, A. J.; Blackwell, A. Insect Physiol. 1993, 39, 903-924.
4. Recent synthetic studies: a) Henry, Jr., K. J.; Fraser-Reid, B. J. Org. Chem. 1994, 59, 5128-5129.
5. b) Kanoh, N.; Ishihara, J.; Murai, A. Synlett 1995, 895-897.
6. Watanabe, H.; Watanabe, T.; Mori, K. Tetrahedron 1996, 52, 13939-13950.
7. See also refs. cited in ref. 2a.
8. Hoppe, D.; Schmincke, H.; Kleemann, H.-W. Tetrahedron 1989, 45, 687-694.
9. Mori, K. Tetrahedron 1974, 30, 3807-3810.
10. Mancuso, A. J.; Huang, S. L.; Swern, D. J. Org. Chem. 1978, 43, 2480-2482.
11. Prepared from cyclopentyl methyl ketone according to the reported procedure; Burton, A.; Hevesi, L.; Dumont, W.; Cravador, A.; Krief, A. Synthesis 1979, 877-880.
12. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156.
13. Davis, F. A.; Vishwakarma, L. C.; Billmers, J. M.; Finn, J. J. Org. Chem. 1984, 49, 3241-3243.
14. Anderson, J. C.; Smith, S. C. Synlett 1990, 107-108.
15. Davis, F. A.; Sheppard, A. C. J. Org. Chem. 1987, 52, 955-957.
16. 2 TLC was also observed by two-dimensional development. On the other hand, in the case of azadirachtin itself, the 5-membered ring hemiacetal structure is stabilized by the hydrogen bonding between the hemiacetal hydroxyl group and the epoxide oxygen of the right hand part.