Synthetic strategies of marine polycyclic ethers via intramolecular allylations: linear and convergent approaches

Acc Chem Res. 2005 May;38(5):423-32. doi: 10.1021/ar040118a.

Abstract

Strategies for the synthesis of polycyclic ethers based on intramolecular allylations are overviewed. The intramolecular condensation of allylic stannanes and aldehydes is a powerful tool for the synthesis of oxepane derivatives. The reaction is successfully applied to the iterative total synthesis of hemibrevetoxin B (2). Further, the intramolecular allylation of alpha-acetoxy ethers provides an efficient method for the convergent synthesis of polycyclic ethers. The usefulness of the latter strategy is demonstrated in the convergent total synthesis of gambierol (4).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • Allyl Compounds / chemical synthesis*
  • Allyl Compounds / chemistry
  • Ethers, Cyclic / chemical synthesis*
  • Ethers, Cyclic / chemistry
  • Molecular Structure
  • Oceans and Seas
  • Polycyclic Compounds / chemical synthesis*
  • Polycyclic Compounds / chemistry

Substances

  • Aldehydes
  • Allyl Compounds
  • Ethers, Cyclic
  • Polycyclic Compounds