Synthesis of Unit A of Cryptophycin via a [2,3]-Wittig Rearrangement
The Journal of Organic Chemistry1999Vol. 64(5), pp. 1459–1463
Citations Over TimeTop 10% of 1999 papers
Jian Liang, David W. Hoard, Vien V. Khau, Michael J. Martinelli, Eric D. Moher, Richard E. Moore, Marcus A. Tius
Abstract
The synthesis of unit A of the cryptophycins from (S)-trans-3-penten-2-ol and from (S)-trans-4-hexen-3-ol has been completed. The key stereodetermining step is a [2,3]-Wittig rearrangement of a propargyl ether. Elaboration of the rearrangement product was accomplished by means of a selective hydroboration-oxidation of a terminal alkyne, Horner-Emmons homologation of the derived aldehyde, followed by selective ozonolytic cleavage and Wittig olefination. This synthesis provides easy access to the series of cryptophycin analogues that incorporate a modified aromatic ring in unit A.
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