Asymmetric total synthesis of pseurotin A

Yujiro Hayashi; Mitsuru Shoji; Shinpei Yamaguchi; Takasuke Mukaiyama; Junichiro Yamaguchi; Hideaki Kakeya; Hiroyuki Osada

doi:10.1021/ol034630s

Asymmetric total synthesis of pseurotin A

Yujiro Hayashi^*, Mitsuru Shoji, Shinpei Yamaguchi, Takasuke Mukaiyama, Junichiro Yamaguchi, Hideaki Kakeya, Hiroyuki Osada

^*Corresponding author for this work

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

58 Citations (Scopus)

Abstract

(Matrix presented) The asymmetric total syntheses of pseurotin A and 8-O-demethylpseurotin A have been accomplished. Key reactions are a NaH-promoted intramolecular cyclization of an alkynylamide to form a γ-lactam, an aldol reaction of a benzylidene-substituted ketone, and the late-stage introduction of the benzoyl group by a selective oxidation of a benzylidene moiety with dimethyldioxirane (DMD).

Original language	English
Pages (from-to)	2287-2290
Number of pages	4
Journal	Organic Letters
Volume	5
Issue number	13
DOIs	https://doi.org/10.1021/ol034630s
Publication status	Published - 2003 Jun 26
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol034630s

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title = "Asymmetric total synthesis of pseurotin A",

abstract = "(Matrix presented) The asymmetric total syntheses of pseurotin A and 8-O-demethylpseurotin A have been accomplished. Key reactions are a NaH-promoted intramolecular cyclization of an alkynylamide to form a γ-lactam, an aldol reaction of a benzylidene-substituted ketone, and the late-stage introduction of the benzoyl group by a selective oxidation of a benzylidene moiety with dimethyldioxirane (DMD).",

author = "Yujiro Hayashi and Mitsuru Shoji and Shinpei Yamaguchi and Takasuke Mukaiyama and Junichiro Yamaguchi and Hideaki Kakeya and Hiroyuki Osada",

year = "2003",

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doi = "10.1021/ol034630s",

language = "English",

volume = "5",

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T1 - Asymmetric total synthesis of pseurotin A

AU - Hayashi, Yujiro

AU - Shoji, Mitsuru

AU - Yamaguchi, Shinpei

AU - Mukaiyama, Takasuke

AU - Yamaguchi, Junichiro

AU - Kakeya, Hideaki

AU - Osada, Hiroyuki

PY - 2003/6/26

Y1 - 2003/6/26

N2 - (Matrix presented) The asymmetric total syntheses of pseurotin A and 8-O-demethylpseurotin A have been accomplished. Key reactions are a NaH-promoted intramolecular cyclization of an alkynylamide to form a γ-lactam, an aldol reaction of a benzylidene-substituted ketone, and the late-stage introduction of the benzoyl group by a selective oxidation of a benzylidene moiety with dimethyldioxirane (DMD).

AB - (Matrix presented) The asymmetric total syntheses of pseurotin A and 8-O-demethylpseurotin A have been accomplished. Key reactions are a NaH-promoted intramolecular cyclization of an alkynylamide to form a γ-lactam, an aldol reaction of a benzylidene-substituted ketone, and the late-stage introduction of the benzoyl group by a selective oxidation of a benzylidene moiety with dimethyldioxirane (DMD).

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U2 - 10.1021/ol034630s

DO - 10.1021/ol034630s

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VL - 5

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EP - 2290

JO - Organic Letters

JF - Organic Letters

IS - 13

ER -

Asymmetric total synthesis of pseurotin A

Abstract

ASJC Scopus subject areas

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