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Biosynthesis-Inspired Approach to Kujounin A2 Using a Stereoselective Tsuji-Trost Alkylation
Alexander Burtea1, Scott D Rychnovsky1
1Department of Chemistry, 1102 Natural Sciences II , University of California at Irvine , Irvine , California 92697 , United States.
Abstract:
A new biosynthesis was proposed for the kujounins A1 and A2 beginning from ascorbic acid, which in turn inspired a synthetic approach to kujounin A2. The ring system was assembled in two steps using a stereoselective Tsuji-Trost reaction followed by ozonolysis. The chemically labile disulfide was introduced in several more steps. These results will make kujounin and its analogues available for further evaluation.
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