Total synthesis of (-)-spinosyn A.
basic_science · Level V
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- Record sourced from PubMed, PMID 15173590.
- Also identified by PMC identifier 514415.
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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.
Medical subject headings
- Macrolides