Formal synthesis of (+)-neooxazolomycin via a Stille cross-coupling/deconjugation route |
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Authors: | Reyhan BastinJames W. Dale Michael G. EdwardsJulien P.N. Papillon Michael R. WebbRichard J.K. Taylor |
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Affiliation: | Department of Chemistry, University of York, Heslington, York, YO10 5AA, UK |
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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. |
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Keywords: | Neooxazolomycin Oxazolomycin Stille coupling Julia-Kocienski Deconjugation Total synthesis |
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