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Published on: February 7, 2019
Synthesis of the Prelog-Djerassi lactone via an asymmetric hydroformylation/crotylation tandem sequence
Roberto M Risi1, Steven D Burke
1Department of Chemistry, University of Wisconsin-Madison , 1101 University Avenue, Madison, Wisconsin 53706-1322, United States.
Abstract:
A synthesis of the Prelog-Djerassi lactone [(+)-1] has been accomplished in three isolations and 57% overall yield from the known vinyl ortho ester 2. A Rh(I)-catalyzed asymmetric hydroformylation/crotylation tandem sequence has been developed and used to set the C2-C4 stereochemistry. A Rh(I)-catalyzed asymmetric hydrogenation was employed to set the C6 sterechemistry, resulting in an unusually short and efficient enantioselective synthesis of this touchstone molecule from achiral starting material.
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