First Total Synthesis of trans- and cis-Resorcylide: Remarkable Hydrogen-Bond-Controlled, Stereospecific Ring-Closing Metathesis
journal contributionposted on 2004-03-18, 00:00 authored by Elias A. Couladouros, Anastasia P. Mihou, Emmanuel A. Bouzas
Stereospecific synthesis of the pair of natural macrolides, trans- and cis-resorcylide, was performed using ring-closing metathesis on dienes 3 and 4, which lack or feature an intramolecular H-bond, respectively. An effective Stille carbonylative coupling of benzyl chlorides 11 and 15 was employed for their preparation. The influence of intramolecular H-bonding on the interconversions of resorcylides was also studied.