Total synthesis of natural (+)-(2's,3'r)-zoapatanol.
[reaction: see text] (+)-Zoapatanol was synthesized by using four key-steps: a Suzuki cross-coupling to prepare a (Z)-alpha,beta-unsaturated ester followed by an enantioselective dihydroxylation to control the C2' and C3' stereocenters, an intramolecular Horner-Wadsworth-Emmons olefination to construct the oxepane ring, and a chemoselective nucleophilic addition/Birch reduction process of a Weinreb amide to introduce simultaneously the beta,gamma-unsaturated ketone on the side-chain and regenerate alcohols from benzyl ethers.
Taillier
Catherine
C
Laboratoire de Chimie Organique, associé au CNRS, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
Bellosta
Véronique
V
Cossy
Janine
J
D001685:Biological Factors / Q000138:chemical synthesis*; D007659:Ketones / Q000138:chemical synthesis; D010082:Oxepins / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds
D001685:Biological Factors; D007659:Ketones; D010082:Oxepins; D014297:Trimethylsilyl Compounds; C442248:zoapatanol; C068554:trimethylsilyl bromide