ChemInform Abstract: Studies on the Synthesis of (-)-Spinosyn A: Application of the Steric Directing Group Strategy to Transannular Diels-Alder Reactions.
ChemInform(2010)
Abstract
A highly diastereoselective and enantioselective synthesis of the decahydro-as-indacene nucleus 12 of (-)-spinosyn A (1) is reported. By implementing the steric directing group strategy, tricyclic lactone 37 was produced from a remarkably diastereoselective transannular Diels-Alder reaction of lactone 9. The tricyclic core of the natural product was then obtained by using an Ireland-Claisen ring contraction of 37. Reversal of the order of these two steps resulted in an almost complete loss of diastereoselectivity.
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Key words
synthesis,steric directing group strategy,cheminform abstract,diels-alder
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