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

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

Research output: Contribution to journalArticle

43 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

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Antineoplastic Antibiotics
Glycyrrhetinic Acid
Stereochemistry
antibiotics
stereochemistry
quinones
Cyclization
Aldehydes
Anti-Bacterial Agents
synthesis
aldehydes
acids
rings
UPA0043
quinone methide
UPA0044
vanillin

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Syntheses and absolute stereochemistries of UPA0043 and UPA0044, cytotoxic antibiotics having a p-quinone-methide structure. / Takao, Kenichi; Sasaki, Tomoko; Kozaki, Tomohito; Yanagisawa, Yumiko; Tadano, Kin Ichi; Kawashima, Akira; Shinonaga, Hideki.

In: Organic Letters, Vol. 3, No. 26, 27.12.2001, p. 4291-4294.

Research output: Contribution to journalArticle

Takao, K, Sasaki, T, Kozaki, T, Yanagisawa, Y, Tadano, KI, Kawashima, A & Shinonaga, H 2001, 'Syntheses and absolute stereochemistries of UPA0043 and UPA0044, cytotoxic antibiotics having a p-quinone-methide structure', Organic Letters, vol. 3, no. 26, pp. 4291-4294. https://doi.org/10.1021/ol016960n
Takao, Kenichi ; Sasaki, Tomoko ; Kozaki, Tomohito ; Yanagisawa, Yumiko ; Tadano, Kin Ichi ; Kawashima, Akira ; Shinonaga, Hideki. / Syntheses and absolute stereochemistries of UPA0043 and UPA0044, cytotoxic antibiotics having a p-quinone-methide structure. In: Organic Letters. 2001 ; Vol. 3, No. 26. pp. 4291-4294.
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