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

Authors
  • Dong, Lin
  • Gordon, Victoria A
  • Grange, Rebecca L
  • Johns, Jenny
  • Parsons, Peter G
  • Porzelle, Achim
  • Reddell, Paul
  • Schill, Heiko
  • Williams, Craig M
Type
Published Article
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society
Publication Date
Nov 19, 2008
Volume
130
Issue
46
Pages
15262–15263
Identifiers
DOI: 10.1021/ja807133p
PMID: 18950180
Source
Medline
License
Unknown

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.

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