First total synthesis of trans- and cis-resorcylide: remarkable hydrogen-bond-controlled, stereospecific ring-closing metathesis

Elias A Couladouros; Anastasia P Mihou; Emmanuel A Bouzas

doi:10.1021/ol0400037

First total synthesis of trans- and cis-resorcylide: remarkable hydrogen-bond-controlled, stereospecific ring-closing metathesis

Org Lett. 2004 Mar 18;6(6):977-80. doi: 10.1021/ol0400037.

Authors

Elias A Couladouros¹, Anastasia P Mihou, Emmanuel A Bouzas

Affiliation

¹ Chemistry Laboratories, Agricultural University of Athens, Iera Odos 75, Athens, 118 55, Greece.

PMID: 15012079
DOI: 10.1021/ol0400037

Abstract

[reaction: see text] 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.