Literature DB >> 15173590

Total synthesis of (-)-spinosyn A.

Dustin J Mergott1, Scott A Frank, William R Roush.   

Abstract

A convergent, highly stereoselective total synthesis of (-)-spinosyn A (1) is described. Key features of the synthesis include the transannular Diels-Alder reaction of macrocyclic pentaene 11 and the transannular Morita-Baylis-Hillman cyclization of 12 that generates tetracycle 26. The total synthesis of (-)-spinosyn A was completed by a sequence involving the highly beta-selective glycosidation reaction of 13 and glycosyl imidate 30.

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Year:  2004        PMID： 15173590      PMCID： PMC514415          DOI： 10.1073/pnas.0401247101

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN： 0027-8424            Impact factor:   11.205


  18 in total

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