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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.

SUBMITTER: Leighty MW

PROVIDER: S-EPMC3138196 | biostudies-literature |

REPOSITORIES: biostudies-literature

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