Palladium-catalyzed stereocontrolled cyclization of 1,3-diene monoepoxide: A route to a new synthetic intermediate for de-ab-cholestane derivative.

Takashi Takahashi; Masahiro Miyazawa; Hiroaki Ueno; Jiro Tsuji

doi:10.1016/S0040-4039(00)83905-2

Palladium-catalyzed stereocontrolled cyclization of 1,3-diene monoepoxide: A route to a new synthetic intermediate for de-ab-cholestane derivative.

Takashi Takahashi^*, Masahiro Miyazawa, Hiroaki Ueno, Jiro Tsuji

^*Corresponding author for this work

Department of Chemistry

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

38 Scopus citations

Abstract

The optically active (2R, 3R)-3-[(3R)-(E)-Benzyloxymethoxy-5-methyl-1-hexenyl]-2-(3-butenyl)-2-methyl-1-cyclopentanone (8) was synthesized as a precursor of vitamin D₃(5) by palladium-catalyzed syn-S_N2′ cyclization of [Z,Z(22S, 23R)]-ene oxide 6 as a key reaction.

Original language	English
Pages (from-to)	3881-3884
Number of pages	4
Journal	Tetrahedron Letters
Volume	27
Issue number	33
DOIs	https://doi.org/10.1016/S0040-4039(00)83905-2
State	Published - 1986

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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@article{117e9139c0044c139c283397908d3cc9,

title = "Palladium-catalyzed stereocontrolled cyclization of 1,3-diene monoepoxide: A route to a new synthetic intermediate for de-ab-cholestane derivative.",

abstract = "The optically active (2R, 3R)-3-[(3R)-(E)-Benzyloxymethoxy-5-methyl-1-hexenyl]-2-(3-butenyl)-2-methyl-1-cyclopentanone (8) was synthesized as a precursor of vitamin D3(5) by palladium-catalyzed syn-SN2′ cyclization of [Z,Z(22S, 23R)]-ene oxide 6 as a key reaction.",

author = "Takashi Takahashi and Masahiro Miyazawa and Hiroaki Ueno and Jiro Tsuji",

year = "1986",

doi = "10.1016/S0040-4039(00)83905-2",

language = "英語",

volume = "27",

pages = "3881--3884",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "33",

}

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T1 - Palladium-catalyzed stereocontrolled cyclization of 1,3-diene monoepoxide

T2 - A route to a new synthetic intermediate for de-ab-cholestane derivative.

AU - Takahashi, Takashi

AU - Miyazawa, Masahiro

AU - Ueno, Hiroaki

AU - Tsuji, Jiro

PY - 1986

Y1 - 1986

N2 - The optically active (2R, 3R)-3-[(3R)-(E)-Benzyloxymethoxy-5-methyl-1-hexenyl]-2-(3-butenyl)-2-methyl-1-cyclopentanone (8) was synthesized as a precursor of vitamin D3(5) by palladium-catalyzed syn-SN2′ cyclization of [Z,Z(22S, 23R)]-ene oxide 6 as a key reaction.

AB - The optically active (2R, 3R)-3-[(3R)-(E)-Benzyloxymethoxy-5-methyl-1-hexenyl]-2-(3-butenyl)-2-methyl-1-cyclopentanone (8) was synthesized as a precursor of vitamin D3(5) by palladium-catalyzed syn-SN2′ cyclization of [Z,Z(22S, 23R)]-ene oxide 6 as a key reaction.

UR - http://www.scopus.com/inward/record.url?scp=0010683289&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(00)83905-2

DO - 10.1016/S0040-4039(00)83905-2

M3 - 学術論文

AN - SCOPUS:0010683289

SN - 0040-4039

VL - 27

SP - 3881

EP - 3884

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 33

ER -

Palladium-catalyzed stereocontrolled cyclization of 1,3-diene monoepoxide: A route to a new synthetic intermediate for de-ab-cholestane derivative.

Abstract

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