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Synthesis of thromboxane B2 via ketalization/ring-closing metathesis
Christopher C Marvin1, Alexander J L Clemens, Steven D Burke
1Department of Chemistry, University of Wisconsin--Madison, 1101 University Avenue, Madison, Wisconsin 53706-1322, USA.
Abstract:
Total synthesis of thromboxane B2 using intermolecular ketalization followed by ring-closing metathesis is reported. Other key steps include a Sharpless asymmetric epoxidation to form an oxirane on the endo face of the bicyclic acetal, epoxide opening using lithioacetonitrile, an allylic alcohol 1,3-transposition, and Mitsunobu lactonization.
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