Enantioselective total synthesis of (+)-testudinariol A using a new nickel-catalyzed allenyl aldehyde cyclization

被引：30

作者：

Amarasinghe, KKD ^{[1
]}

Montgomery, J ^{[1
]}

机构：

[1] Wayne State Univ, Dept Chem, Detroit, MI 48202 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 32期

关键词：

D O I：

10.1021/ja027148y

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An enantioselective total synthesis of (+)-testudinariol A was completed. A new nickel-catalyzed allenyl aldehyde cyclization was developed in the approach. In addition, an asymmetric anti aldol reaction and a two-directional oxocarbenium ion/vinyl silane condensation were employed as key steps. Copyright © 2002 American Chemical Society.

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页码：9366 / 9367

页数：2

相关论文

共 20 条

[1] The anti-selective boron-mediated asymmetric aldol reaction of carboxylic esters [J].

Abiko, A ;

Liu, JF ;

Masamune, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (10) :2586-2587

[2] VINYLSILANE-TERMINATED AND ALKYNYLSILANE-TERMINATED CYCLIZATION REACTIONS [J].

BLUMENKOPF, TA ;

OVERMAN, LE .

CHEMICAL REVIEWS, 1986, 86 (05) :857-873

[3] PREPARATION OF 7-MEMBERED-RING CYCLIC ETHERS AND 3-ALKYLIDENETETRAHYDROPYRANS FROM THE CYCLIZATION OF OXONIUM CATIONS DERIVED FROM UNSUBSTITUTED AND SILICON-CONTAINING 4-ALKEN-1-OLS [J].

CASTANEDA, A ;

KUCERA, DJ ;

OVERMAN, LE .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (24) :5695-5707

[4] A stereodivergent approach to (-)-α-kainic acid and (+)-α-allokainic acid utilizing the complementarity of alkyne and allene cyclizations [J].

Chevliakov, MV ;

Montgomery, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (48) :11139-11143

[5]

Hioki H, 2001, CHEM LETT, P898

[6] 2-DIRECTIONAL SYNTHESIS AND ITS USE IN NATURAL PRODUCT SYNTHESIS [J].

MAGNUSON, SR .

TETRAHEDRON, 1995, 51 (08) :2167-2213

[7] STEREOSELECTIVE TRISUBSTITUTED OLEFIN SYNTHESIS VIA VINYLSILANES [J].

MILLER, RB ;

MCGARVEY, G .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (25) :4623-4633

[8] A new stereoselective method for the preparation of allylic alcohols [J].

Oblinger, E ;

Montgomery, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (38) :9065-9066

[9] Ti(II)-mediated tandem inter- and intramolecular coupling reaction of unsaturated hydrocarbons: One-pot preparation of cyclopentanes and cyclohexanes from readily available acyclic starting materials [J].

Okamoto, S ;

Subburaj, K ;

Sato, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (20) :4857-4858

[10] ACETAL-INITIATED CYCLIZATIONS OF VINYLSILANES - A GENERAL-SYNTHESIS OF ALLYLICALLY UNSATURATED OXACYCLICS [J].

OVERMAN, LE ;

CASTANEDA, A ;

BLUMENKOPF, TA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (06) :1303-1304