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Formal synthesis of (+)-neooxazolomycin via a Stille cross-coupling/deconjugation route
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| Journal | Tetrahedron |
|---|---|
| Date | Published - 23 Dec 2011 |
| Issue number | 51 |
| Volume | 67 |
| Number of pages | 19 |
| Pages (from-to) | 10026-10044 |
| Original language | English |
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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