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

doi:10.1021/ol016960n

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

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

60 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 language	English
Pages (from-to)	4291-4294
Number of pages	4
Journal	Organic Letters
Volume	3
Issue number	26
DOIs	https://doi.org/10.1021/ol016960n
Publication status	Published - 2001 Dec 27

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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

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.",

author = "Takao, {Ken Ichi} and Tomoko Sasaki and Tomohito Kozaki and Yumiko Yanagisawa and Tadano, {Kin Ichi} and Akira Kawashima and Hideki Shinonaga",

year = "2001",

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language = "English",

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T1 - Syntheses and absolute stereochemistries of UPA0043 and UPA0044, cytotoxic antibiotics having a p-quinone-methide structure

AU - Takao, Ken Ichi

AU - Sasaki, Tomoko

AU - Kozaki, Tomohito

AU - Yanagisawa, Yumiko

AU - Tadano, Kin Ichi

AU - Kawashima, Akira

AU - Shinonaga, Hideki

PY - 2001/12/27

Y1 - 2001/12/27

N2 - (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.

AB - (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.

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JO - Organic Letters

JF - Organic Letters

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ER -

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

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ASJC Scopus subject areas

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