1394253-72-5Relevant academic research and scientific papers
Non-canonical regioisomerizations and a 'Diels-Alderase' are likely essential in the biosynthesis of Spiculoic acid A
Pinto, Atahualpa,Boddy, Christopher N.
, p. 5253 - 5256 (2012/09/07)
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.
