724422-96-2Relevant academic research and scientific papers
Synthetic approaches and total synthesis of natural zoapatanol
Taillier, Catherine,Gille, Barbara,Bellosta, Veronique,Cossy, Janine
, p. 2097 - 2108 (2007/10/03)
(Chemical Equation Presented) The total synthesis of (+)-zoapatanol utilizing an intramolecular Horner-Wadsworth-Emmons olefination and an enantioselective Sharpless dihydroxylation as the key steps has been achieved. An advanced oxepene intermediate has been obtained by applying a ring-closing metathesis to an unsaturated enol ether.
Total synthesis of natural (+)-(2′S,3′R)-zoapatanol
Taillier, Catherine,Bellosta, Veronique,Cossy, Janine
, p. 2149 - 2151 (2007/10/03)
(+)-Zoapatanol was synthesized by using four key-steps: a Suzuki cross-coupling to prepare a (Z)-α,β-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 β,γ-unsaturated ketone on the side-chain and regenerate alcohols from benzyl ethers.
