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[SANET-MG] spinosynA of spinosad is synthesized



The article below is both good news and bad news for organic
agriculture. The good news is that  a main ingredient in the organic
insecticide spinosad has been  characterized. The bad news is that the
synthesis will probably lead to numerous synthetic copies that will pose
a dilemma for  organic approval.
Published online before print June 1, 2004
Proc. Natl. Acad. Sci. USA, 10.1073/pnas.0401247101

Total synthesis of (-)-spinosyn A

Dustin J. Mergott, Scott A. Frank *, and William R. Roush
Department of Chemistry, University of Michigan, Ann Arbor, MI 48109

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 -selective glycosidation reaction of 13 and
glycosyl imidate 30.

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