Structure and absolute stereochemistry of the anticancer agent EBC-23 from the Australian rainforest

J Am Chem Soc. 2008 Nov 19;130(46):15262-3. doi: 10.1021/ja807133p. Epub 2008 Oct 25.

Abstract

EBC-23 (2), a prostate anticancer agent, was isolated from the fruit of Cinnamomum laubatii (family Lauraceae) in the Australian tropical rainforest. Extensive NOE experiments enabled the relative stereochemistry of the proposed EBC-23 (2) structure to be determined. Total synthesis of both enantiopodes over nine linear steps, involving challenging RCM and spiroacetal cyclizations, confirmed the gross structure and relative and absolute stereochemistry.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Australia
  • Cinnamomum / chemistry
  • Climate*
  • Molecular Structure
  • Pyrans / chemical synthesis
  • Pyrans / chemistry*
  • Rain*
  • Spiro Compounds / chemical synthesis
  • Spiro Compounds / chemistry*
  • Stereoisomerism
  • Trees*

Substances

  • Antineoplastic Agents
  • EBC-23
  • Pyrans
  • Spiro Compounds