Synthetic studies on hemicalide: development of a convergent approach toward the C1-C25 fragment

Org Lett. 2013 Sep 20;15(18):4734-7. doi: 10.1021/ol402077e. Epub 2013 Sep 3.

Abstract

Synthetic studies on hemicalide, a recently isolated marine natural product displaying highly potent antiproliferative activity and a unique mode of action, have highlighted a reliable Horner-Wadsworth-Emmons olefination to create the C6-C7 alkene and a remarkable efficient Suzuki-Miyaura coupling to form the C15-C16 bond, resulting in the development of a convergent approach toward the C1-C25 fragment.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Biological Products / pharmacology
  • Marine Biology
  • Molecular Structure
  • Polyketides / chemical synthesis*
  • Polyketides / chemistry
  • Polyketides / pharmacology
  • Porifera / chemistry
  • Stereoisomerism

Substances

  • Alkenes
  • Antineoplastic Agents
  • Biological Products
  • Polyketides
  • hemicalide