Syntheses and Absolute Stereochemistries of UPA0043 and UPA0044, Cytotoxic Antibiotics Having a p-Quinone-methide Structure

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 sy...

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Bibliographic Details
Published in:Organic letters 2001-12, Vol.3 (26), p.4291-4294
Main Authors: Takao, Ken-ichi, Sasaki, Tomoko, Kozaki, Tomohito, Yanagisawa, Yumiko, Tadano, Kin-ichi, Kawashima, Akira, Shinonaga, Hideki
Format: Article
Language:English
Subjects:
Antibiotics, Antineoplastic - chemical synthesis
Antibiotics, Antineoplastic - chemistry
Antibiotics, Antineoplastic - pharmacology
Indolequinones
Indoles - chemistry
Molecular Structure
Quinones - chemical synthesis
Quinones - chemistry
Quinones - pharmacology
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol016960n