A simple but remarkably effective device for forming the C8-C14 polycyclic ring system of halichondrin B

J Am Chem Soc. 2004 Jun 30;126(25):7770-1. doi: 10.1021/ja047826b.

Abstract

A simple device consisting of two ion-exchange columns, two alumina-based filters, and a pump (Figure 1) was assembled to form the C8-C14 polycyclic ring system present in the halichondrin B class of marine natural products. The effectiveness of this device was tested for three substrates. In each case, the desired polycyclic ketal 3, 5, or 7 was obtained almost quantitatively in a single operation.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Aldehydes / chemistry
  • Animals
  • Cyclization
  • Ethers, Cyclic / chemical synthesis*
  • Ethers, Cyclic / chemistry
  • Ketones / chemistry
  • Macrolides
  • Molecular Structure
  • Oxidation-Reduction
  • Porifera / chemistry
  • Stereoisomerism

Substances

  • Aldehydes
  • Ethers, Cyclic
  • Ketones
  • Macrolides
  • halichondrin B