2. Academic Validation
  3. Total Syntheses and Cytotoxicity of (R)- and (S)-Boehmeriasin A

Total Syntheses and Cytotoxicity of (R)- and (S)-Boehmeriasin A

  • ACS Med Chem Lett. 2011 Apr 14;2(4):313-315. doi: 10.1021/ml1003074.
Matthew W Leighty 1,  Gunda I Georg
Affiliations

Affiliation

  • 1 Department of Medicinal Chemistry, The University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045 and Department of Medicinal Chemistry and The Institute for Therapeutics Discovery and Development, University of Minnesota, 717 Delaware Street SE, Minneapolis, Minnesota 55414.
PMID: 21779519 DOI: 10.1021/ml1003074
Abstract

Both enantiomers of boehmeriasin A were synthesized in seven steps each, using a chiral pool approach. Key steps in the synthesis are a one-flask, two-step protocol to generate the quinolizine core and a C-H functionalization reaction between tetrahydroquinolizinones and an aryltrifluoroborate. The natural product (R)-boehmeriasin A demonstrated potent cytotoxicity against several Cancer cell lines, whereas the unnatural (+)-(S)-isomer was significantly less potent.

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