Stereoselective synthesis of eight-membered cyclic ethers by tandem Nicholas reaction/ring-closing metathesis: a short synthesis of (+)-cis-Lauthisan

Org Lett. 2006 Mar 2;8(5):871-3. doi: 10.1021/ol052932j.

Abstract

Cis-2,8-disubstituted oxocanes and the parent unsaturated precursors were prepared from the corresponding Co2(CO)6-cycloalkynic ethers. Key steps in such synthesis were the ether linkage formation by intermolecular Nicholas reaction, RCM of the suitable acyclic dienyl ether and montmorillonite K-10 induced isomerization of the complexed cycloalkyne. A short synthesis of (+)-cis-lauthisan taking advantage of the developed methodology is described.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclization
  • Ethers, Cyclic / chemical synthesis*
  • Ethers, Cyclic / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • Ethers, Cyclic
  • lauthisan