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Formal synthesis of (+)-neooxazolomycin via a Stille cross-coupling/deconjugation route

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JournalTetrahedron
DatePublished - 23 Dec 2011
Issue number51
Volume67
Number of pages19
Pages (from-to)10026-10044
Original languageEnglish

Abstract

A formal synthesis of neooxazolomycin is described via the preparation of Kende's key intermediate in a longest linear sequence of 23 steps. This work is founded upon the union of three fragments: Moloney's lactam-derived triflate, a vinyl stannane and a Julia-Kocienski sulfone and encompasses three key steps: (i) a Stille cross-coupling to combine the triflate and vinyl stannane, (ii) a base-promoted enone deconjugation to derive the dihydroxylation precursor and (iii) our previously reported Julia-Kocienski methodology to assemble the pentadienyl amine side chain with the sulfone precursor. (C) 2011 Elsevier Ltd. All rights reserved.

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