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Synthesis and evaluation of the cytotoxicity of apoptolidinones A and D.

Authors
  • Ghidu, Victor P1
  • Wang, Jingqi
  • Wu, Bin
  • Liu, Qingsong
  • Jacobs, Aaron
  • Marnett, Lawrence J
  • Sulikowski, Gary A
  • 1 Department of Chemistry, Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37235-1822, USA.
Type
Published Article
Journal
The Journal of Organic Chemistry
Publisher
American Chemical Society
Publication Date
Jul 04, 2008
Volume
73
Issue
13
Pages
4949–4955
Identifiers
DOI: 10.1021/jo800545r
PMID: 18543990
Source
Medline
License
Unknown

Abstract

Apoptolidins A-D are microbial secondary metabolites shown to be selectively cytotoxic against several cancer cell lines and noncytotoxic against normal cells. Total syntheses of apoptolidinones A and D are reported. The efficient synthetic strategy leading to the apoptolidinones features construction of the common 20-membered macrolactone by an intramolecular Suzuki reaction and stereocontrolled aldol reactions establishing the C19/C20 and C22/C23 stereocenters. In contrast to apoptolidin A, the aglycones apoptolidinone A and D were shown to be noncytotoxic when evaluated against human lung cancer cells (H292).

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