Syntheses and absolute stereochemistries of UPA0043 and UPA0044, cytotoxic antibiotics having a p-quinone-methide structure

Ken Ichi Takao, Tomoko Sasaki, Tomohito Kozaki, Yumiko Yanagisawa, Kin Ichi Tadano, Akira Kawashima, Hideki Shinonaga

Research output: Contribution to journalArticle

47 Citations (Scopus)

Abstract

(Formula Presented) The first syntheses of new antibiotics UPA0043 and UPA0044 were accomplished starting from commercially available 18β-glycyrrhetinic acid and vanillin. The present syntheses involve the coupling of a sesquiterpenoid aldehyde and an aryllithium, the stereoselective formation of a p-quinone-methide system, and regioselective intramolecular cyclization via an epoxy ring opening.

Original languageEnglish
Pages (from-to)4291-4294
Number of pages4
JournalOrganic Letters
Volume3
Issue number26
DOIs
Publication statusPublished - 2001 Dec 27

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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