Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1371258 | Bioorganic & Medicinal Chemistry Letters | 2012 | 4 Pages |
Abstract
The regiochemistry of dehydration and cyclization steps of the linear biosynthetic precursor of the polyketide natural product Spiculoic acid A (1) were examined. Herein we describe the synthesis of polyene-containing aldehyde 21, a counterpart to the metabolite’s putative polyketide intermediate and demonstrate its inability to undergo facile IMDA chemistry. These results suggest the involvement of a non-canonical regioisomerization in the biosynthesis of 1, and that the IMDA reaction is likely enzyme-catalyzed.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Atahualpa Pinto, Christopher N. Boddy,