Catalytic asymmetric total syntheses of quinine and quinidine

被引：164

作者：

Raheem, IT ^{[1
]}

Goodman, SN ^{[1
]}

Jacobsen, EN ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 03期

关键词：

D O I：

10.1021/ja039550y

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The catalytic, asymmetric syntheses of quinine and quinidine were achieved in 16 steps. The recently developed salen(Al)-catalyzed enantioselective Michael addition of methyl cyanoacetate served to set the crucial C4 stereocenter in 92% ee, and a late-stage asymmetric dihydroxylation was used to differentiate the common intermediate and access the two desired diastereomeric products with high selectivity. Copyright © 2004 American Chemical Society.

引用

页码：706 / 707

页数：2

共 26 条

[1]

Aggarwal VK, 2001, ANGEW CHEM INT EDIT, V40, P1430, DOI 10.1002/1521-3773(20010417)40:8<1430::AID-ANIE1430>3.0.CO

[2]

2-W

[3] Fast and efficient synthesis of novel fumagillin analogues [J].

Baldwin, JE ;

Bulger, PG ;

Marquez, R .

TETRAHEDRON, 2002, 58 (27) :5441-5452

[4] STEREOSPECIFIC SYNTHESIS OF ERYTHRO-CINCHONA ALKALOIDS FROM SECOLOGANIN [J].

BROWN, RT ;

CURLESS, D .

TETRAHEDRON LETTERS, 1986, 27 (49) :6005-6008

[5] EFFECT OF CHIRAL QUATERNARY AMMONIUM-SALTS ON (SALEN)MN-CATALYZED EPOXIDATION OF CIS-OLEFINS - A HIGHLY ENANTIOSELECTIVE, CATALYTIC ROUTE TO TRANS-EPOXIDES [J].

CHANG, SB ;

GALVIN, JM ;

JACOBSEN, EN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (15) :6937-6938

[6]

Goodman SN, 2002, ADV SYNTH CATAL, V344, P953, DOI 10.1002/1615-4169(200210)344:9<953::AID-ADSC953>3.0.CO

[7]

2-A

[8]

Grethe G., 1983, CHEM HETEROCYCLIC 4, V23, P279

[9] TOTAL SYNTHESIS OF CINCHONA ALKALOIDS .2. STEREOSELECTIVE TOTAL SYNTHESES OF QUININE AND QUINIDINE [J].

GUTZWILLER, J ;

USKOKOVIC, MR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (02) :576-581

[10]

Kacprzak K, 2001, SYNTHESIS-STUTTGART, P961

← 1 2 3 →