Construction of the Benzylic Quaternary Carbon Center of Zoanthenol by Intramolecular Mizoroki - Heck Reaction of Enone

Go Hirai; Yuuki Koizumi; Sameh M. Moharram; Hiroki Oguri; Masahiro Hirama

doi:10.1021/ol025852d

Construction of the Benzylic Quaternary Carbon Center of Zoanthenol by Intramolecular Mizoroki - Heck Reaction of Enone

Go Hirai, Yuuki Koizumi, Sameh M. Moharram, Hiroki Oguri, Masahiro Hirama

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

28 Citations (Scopus)

Abstract

(matrix presented) Stereocontrolled synthesis of the ABC ring framework of zoanthenol has been achieved. Our studies show that a ββ-substituted enone can act as a good acceptor of arylpalladium intermediates in the formation of a congested benzylic quaternary carbon center through an intramoleculer Mizoroki-Heck reaction. The cis B/C ring system was stereoselectively converted to the trans-fused framework through a Sml₂-promoted deoxygenation of the α-hydroxy ketone.

Original language	English
Pages (from-to)	1627-1630
Number of pages	4
Journal	Organic Letters
Volume	4
Issue number	9
DOIs	https://doi.org/10.1021/ol025852d
Publication status	Published - May 2 2002
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol025852d

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abstract = "(matrix presented) Stereocontrolled synthesis of the ABC ring framework of zoanthenol has been achieved. Our studies show that a ββ-substituted enone can act as a good acceptor of arylpalladium intermediates in the formation of a congested benzylic quaternary carbon center through an intramoleculer Mizoroki-Heck reaction. The cis B/C ring system was stereoselectively converted to the trans-fused framework through a Sml2-promoted deoxygenation of the α-hydroxy ketone.",

author = "Go Hirai and Yuuki Koizumi and Moharram, {Sameh M.} and Hiroki Oguri and Masahiro Hirama",

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T1 - Construction of the Benzylic Quaternary Carbon Center of Zoanthenol by Intramolecular Mizoroki - Heck Reaction of Enone

AU - Hirai, Go

AU - Koizumi, Yuuki

AU - Moharram, Sameh M.

AU - Oguri, Hiroki

AU - Hirama, Masahiro

PY - 2002/5/2

Y1 - 2002/5/2

N2 - (matrix presented) Stereocontrolled synthesis of the ABC ring framework of zoanthenol has been achieved. Our studies show that a ββ-substituted enone can act as a good acceptor of arylpalladium intermediates in the formation of a congested benzylic quaternary carbon center through an intramoleculer Mizoroki-Heck reaction. The cis B/C ring system was stereoselectively converted to the trans-fused framework through a Sml2-promoted deoxygenation of the α-hydroxy ketone.

AB - (matrix presented) Stereocontrolled synthesis of the ABC ring framework of zoanthenol has been achieved. Our studies show that a ββ-substituted enone can act as a good acceptor of arylpalladium intermediates in the formation of a congested benzylic quaternary carbon center through an intramoleculer Mizoroki-Heck reaction. The cis B/C ring system was stereoselectively converted to the trans-fused framework through a Sml2-promoted deoxygenation of the α-hydroxy ketone.

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JO - Organic Letters

JF - Organic Letters

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ER -

Construction of the Benzylic Quaternary Carbon Center of Zoanthenol by Intramolecular Mizoroki - Heck Reaction of Enone

Abstract

All Science Journal Classification (ASJC) codes

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