Synthesis of taxane A/B ring by intramolecular nitrile oxide cyclization reaction

Tetrahedron Letters

Volumn 38, Issue 11, 1997, Pages 1969-1970

  Hirai, Yoshimasa ^a   Nagaoka, Hiroto ^a  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

TAXANE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0031575740     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00236-0     Document Type: Article

References (21)

1. 1. This paper is dedicated to Prof. Yoshito Kishi on the occasion of his 60th birthday.
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16. 4NF/THF; 3) CDI, NaH/THF-DMF (50% overall yield from 6)
17. 3) δ 7.76 (1H, m), 7.27-7.30 (2H, m), 7.19 (1H, m), 5.35 (1H, s), 5.06 (1H, s), 4.56 (2H, t, J=7.7 Hz), 3.64 (1H, dt, J=14.1, 7.7 Hz), 3.38 (1H, dt, J=14.1, 7.7 Hz), 2.04-2.15 (2H, m) 1.80 (1H, m), 1.60 (3H, s), 1.49 (3H, s), 1.48 (3H, s), 1.39 (1H, m), 1.22 (3H, s), 0.92 (3H, s).
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19. ++H).
20. 13 Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467. MM2 calculation of 13 was carried out using the acetylene unit for the nitrile oxide unit.
21. 14 This work was partially supported by a Special Grant from Meiji College of Pharmacy which is gratefully acknowledged. Tetrahedron Letters, Vol. 38, No. 11, pp. 1865-1868, 1997