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A Highly Stereoselective, Efficient, and Scalable Synthesis of the C(1)–C(9) Fragment of the Epothilones

Author:
Foley, Corinne N., Leighton, James L.
Source:
Organic letters 2015 v.17 no.23 pp. 5858-5861
ISSN:
1523-7052
Subject:
alcohols, chemical structure, diastereoselectivity, oxidation
Abstract:
A second-generation synthesis of the C(1)–C(9) fragment of the epothilones is reported. The key tandem intramolecular silylformylation/crotylsilylation/“aprotic” Tamao oxidation sequence has been redeveloped as a stepwise intermolecular variant, allowing excellent levels of diastereoselectivity in the crotylation step and proceeds in 50% overall yield on gram scale. An improved synthesis of the homopropargyl alcohol starting material is also described, which proceeds in four steps and >99% ee from inexpensive starting materials and is amenable to multigram scales.
Agid:
5789979