Sequencing olefination reactions: application toward the total synthesis of (+)-crocacin C

ORGN 123

Gopal Sirasani, Tapas Paul, and Rodrigo B. Andrade, randrade@temple.edu. Department of Chemistry, Temple University, 1901 N. 13th Street, Philadelphia, PA 19122
The utility of intra- and intermolecular olefin metathesis in total synthesis has been well established. Herein we present (1) tandem cross-metathesis/Wittig or Horner-Wadsworth-Emmons olefination methodology for the stereoselective synthesis of both (2E,4E)- and (2Z,4E)-dienoates; and (2) an efficient strategy for natural product synthesis which sequences allyl- or crotylmetallation reactions with olefin cross metathesis. Application of the latter towards a concise total synthesis of (+)-crocacin C will be discussed.