Synthesis of thromboxane B2 via ketalization/ring-closing metathesis.

Org Lett

Department of Chemistry, University of Wisconsin--Madison, 1101 University Avenue, Madison, Wisconsin 53706-1322, USA.

Published: December 2007

AI Article Synopsis

  • A total synthesis of thromboxane B2 is achieved using an innovative approach that includes intermolecular ketalization and ring-closing metathesis.
  • Key methods in this synthesis involve Sharpless asymmetric epoxidation to create an oxirane, followed by epoxide opening with lithioacetonitrile.
  • Additional transformations include an allylic alcohol 1,3-transposition and Mitsunobu lactonization to finalize the synthesis.

Article 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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Source
http://dx.doi.org/10.1021/ol7021214DOI Listing

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