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Stereoselektive Synthesen von Taxan‐Derivaten
Author(s) -
Neh Harribert,
Kühling Andrea,
Blechert Siegfried
Publication year - 1989
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19890720113
Subject(s) - chemistry , stereoselectivity , aldol reaction , stereochemistry , taxane , acetal , hydrolysis , organic chemistry , catalysis , medicine , cancer , breast cancer
Stereoselective Synthesis of Taxane Derivatives Substituted racemic 4,8,12‐trinortaxanes were prepared stereoselectively in several steps from the dienone 10 . A variant of the de Mayo reaction with bicyclononenones 4 and cyclohexen produced the desired configuration at C(8) of the taxane framework. Retro ‐aldol cleavage of the tetracycle 5 led to the taxane skeleton 6 . Stereoselective reduction followed by treatment with base afforded 7b . Hydrolysis of the acetal group and further reduction yielded 9 in which the relative configuration corresponds to the one of the natural products.