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

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研究成果: Article › 査読

60 被引用数 (Scopus)

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(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.

本文言語	English
ページ（範囲）	4291-4294
ページ数	4
ジャーナル	Organic Letters
巻	3
号	26
DOI	https://doi.org/10.1021/ol016960n
出版ステータス	Published - 2001 12月 27

ASJC Scopus subject areas

生化学
物理化学および理論化学
有機化学

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10.1021/ol016960n

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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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day = "27",

doi = "10.1021/ol016960n",

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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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U2 - 10.1021/ol016960n

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JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 26

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

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