Total syntheses and cytotoxicity of (R)- and (S)-boehmeriasin A

Matthew W. Leighty, Gunda I. Georg

Research output: Contribution to journalArticlepeer-review

29 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)313-315
Number of pages3
JournalACS Medicinal Chemistry Letters
Volume2
Issue number4
DOIs
StatePublished - Apr 14 2011

Keywords

  • Natural product synthesis
  • boehmeriasin A
  • cytotoxicity
  • drug resistance
  • phenanthroquinolizidine

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