Catalyzed asymmetric Diels-Alder reactions of benzoquinone. totalsynthesis of (-)-ibogamine

被引：31

作者：

White, JD ^{[1
]}

Choi, YG ^{[1
]}

机构：

[1] Oregon State Univ, Dept Chem, Corvallis, OR 97331 USA

来源：

HELVETICA CHIMICA ACTA | 2002年 / 85卷 / 12期

关键词：

D O I：

10.1002/hlca.200290014

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The Diels-Alder reaction of 1.4-benzoquinone with 1.3-dienes catalyzed by Mikami's [Ti{(S)-binol(2 -)}Cl;] complex (binoi = [1.1 binaphthalene]-2.2 -diol) gives cycloadducts in good yield and in high enantiomer excess. A model is proposed to explain the observed absolute Configuration of cycloadducts and the reaction is used as the key step in an asymmetric synthesis leading to the alkaloid ( )-ibogamine.

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页码：4306 / 4327

页数：22

相关论文

共 60 条

[1] Free radical cyclizations in alkaloid total synthesis: (+/-)-21-oxogelsemine and (+/-)-gelsemine [J].

Atarashi, S ;

Choi, JK ;

Ha, DC ;

Hart, DJ ;

Kuzmich, D ;

Lee, CS ;

Ramesh, S ;

Wu, SC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (27) :6226-6241

[2]

ATTAURRAHMAN JA, 1980, TETRAHEDRON, V36, P1063

[3] THE ALKALOIDS OF TABERNANTHE-IBOGA .4. THE STRUCTURES OF IBOGAMINE, IBOGAINE, TABERNANTHINE AND VOACANGINE [J].

BARTLETT, MF ;

DICKEL, DF ;

TAYLOR, WI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (01) :126-136

[4]

BESWICK PJ, 1985, SYNTHESIS-STUTTGART, P492

[5]

BJORKLING F, 1987, J ORG CHEM, V52, P292

[6] ALKALOIDS .30. CHIROPTICAL INVESTIGATIONS ON IBOGA AND VOACANGA ALKALOIDS [J].

BLAHA, K ;

KOBLICOV.Z ;

TROJANEK, J .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1974, 39 (08) :2258-2266

[7] Catalytic enantioselective Diels-Alder reactions of 1,4-quinone monoketals [J].

Breuning, M ;

Corey, EJ .

ORGANIC LETTERS, 2001, 3 (10) :1559-1562

[8] CATECHOLBORANE (1,3,2-BENZODIOXABOROLE) AS A NEW, GENERAL MONOHYDROBORATION REAGENT FOR ALKYNES - CONVENIENT SYNTHESIS OF ALKENEBORONIC ESTERS AND ACIDS FROM ALKYNES VIA HYDROBORATION [J].

BROWN, HC ;

GUPTA, SK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (12) :4370-&

[9] TOTAL SYNTHESIS OF (+-)-IBOGAMINE AND OF (+-)-EPIIBOGAMINE [J].

BUCHI, G ;

COFFEN, DL ;

KOCSIS, K ;

SONNET, PE ;

ZIEGLER, FE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (09) :2073-&

[10] TOTAL SYNTHESIS OF IBOGA ALKALOIDS [J].

BUCHI, G ;

COFFEN, DL ;

KOCSIS, K ;

SONNET, PE ;

ZIEGLER, FE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (13) :3099-&

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