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

Both enantiomers of boehmeriasin A were synthesized in seven steps each using a chiral pool approach. Key steps in the syntheses are a one-flask, two-step protocol to generate the quinolizine core and a C−H functionalization reaction between tetrahydroquinolizinones and an aryltrifluoroborate. The n...

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Published inACS medicinal chemistry letters Vol. 2; no. 4; pp. 313 - 315
Main Authors Leighty, Matthew W, Georg, Gunda I
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 14.04.2011
Subjects
Letter
phenanthroquinolizidine
drug resistance
Natural product synthesis
boehmeriasin A
cytotoxicity
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Summary:Both enantiomers of boehmeriasin A were synthesized in seven steps each using a chiral pool approach. Key steps in the syntheses 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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ISSN:1948-5875
1948-5875
DOI:10.1021/ml1003074