A concise route to (-)-kainic acid

被引：51

作者：

Nakagawa, H ^{[1
]}

Sugahara, T ^{[1
]}

Ogasawara, K ^{[1
]}

机构：

[1] Tohoku Univ, Inst Pharmaceut, Sendai, Miyagi 9808578, Japan

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 20期

关键词：

D O I：

10.1021/ol006377r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A concise route to (-)-kainic acid from enantiopure (+)-cis-4-carbobenzoxyamino-2-cyclopentenol has been devised by employing concurrent Chugaev syn-elimination and intramolecular ene reaction as the key step.

引用

页码：3181 / 3183

页数：3

共 22 条

[1] Enantioselective total synthesis of (-)-alpha-kainic acid through free radical cyclization of an alkenyl monothioformimide [J].

Bachi, MD ;

Melman, A .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (06) :1896-1898

[2] The total synthesis of (-)-α-kainic acid using titanium-mediated diene metallabicyclisation methodology [J].

Campbell, AD ;

Raynham, TM ;

Taylor, RJK .

CHEMICAL COMMUNICATIONS, 1999, (03) :245-246

[3] 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

[4] Approaches to a synthesis of α-kainic acid [J].

Cossy, J ;

Cases, M ;

Pardo, DG .

TETRAHEDRON, 1999, 55 (19) :6153-6166

[5]

CURRUTHERS W, 1990, CYCLOADDITION REACTI, P252

[6] Stereoselective synthesis of (-)-alpha-kainic acid and (+)-alpha-allokainic acid via trimethylstannyl-mediated radical carbocyclization and oxidative destannylation [J].

Hanessian, S ;

Ninkovic, S .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) :5418-5424

[7]

Hashimoto K, 1991, TRENDS ORGANIC CHEM, V2, P1

[8]

KAMIKUBO T, 1995, CHEM COMMUN, P1951

[9]

Kawamura M, 1997, HETEROCYCLES, V44, P129

[10]

Miyata O, 1997, SYNLETT, P275

← 1 2 3 →