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

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.

• Authors: Matthew W Leighty, Gunda I Georg
• Journal: ACS medicinal chemistry letters (ACS Med Chem Lett) Vol. 2 Issue 4 Pg. 313-315 (Apr 14 2011) ISSN: 1948-5875 [Print] United States
• PMID: 21779519 (Publication Type: Journal Article)