Org Lett. 2010 Jul 16;12(14):3192-5.

Exploring the original proposed biosynthesis of (+)-symbioimine: remote exocyclic stereocontrol in a type I IMDA reaction.

Burke JP, Sabat M, Iovan DA, Myers WH, Chruma JJ.

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Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904, USA.

Abstract

The originally proposed biosynthesis of (+)-symbioimine was explored, resulting in the successful intramolecular Diels-Alder (IMDA) cyclization of an appropriate (E,E,E)-1,7,9-decatrien-3-one. In contrast to the originally proposed biosynthesis, the IMDA reaction appears to proceed via an endo transition state. Remarkably, a single exocyclic stereogenic center effectively controls the pi-facial selectivity affording a highly diastereoselective cycloaddition.

PMID:: 20550217; [PubMed - indexed for MEDLINE]

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