An approach to the isoschizozygane alkaloid core using a 1,4-dipolar cycloaddition of a cross-conjugated heteroaromatic betaine

被引：38

作者：

Padwa, A ^{[1
]}

Flick, AC ^{[1
]}

Lee, HI ^{[1
]}

机构：

[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 14期

关键词：

D O I：

10.1021/ol0508779

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new strategy for the synthesis of the isoschizozygane alkaloid core has been developed that is based on a 1,4-dipolar cycloaddition reaction of a cross-conjugated heteroaromatic betaine. The resulting cycloadduct undergoes loss of COS, and further reduction delivers a 5a-aza-acenaphthylene intermediate that was transformed into the isoschizozygane skeleton upon treatment with acid.

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页码：2925 / 2928

页数：4

相关论文

共 31 条

[1] MODIFIED MOLYBDENUM CARBONYL SPECIES - EXCELLENT REAGENTS FOR THE DESULFURIZATION OF THIOLS [J].

ALPER, H ;

BLAIS, C .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (04) :169-170

[2] RULES FOR RING-CLOSURE [J].

BALDWIN, JE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736

[3] REACTION OF SODIUM BOROHYDRIDE WITH NICKEL ACETATE IN AQUEOUS SOLUTION-A CONVENIENT SYNTHESIS OF AN ACTIVE NICKEL HYDROGENATION CATALYST OF LOW ISOMERIZING TENDENCY [J].

BROWN, CA ;

BROWN, HC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (07) :1003-&

[4]

Deslongchamps P., 1983, Stereoelectronic Effects in Organic Chemistry

[5] 6-MEMBERED MESOIONIC HETEROCYCLES OF THE META-QUINODIMETHANE DIANION TYPE [J].

FRIEDRICHSEN, W ;

KAPPE, T ;

BOTTCHER, A .

HETEROCYCLES, 1982, 19 (06) :1083-1148

[6] Revised structure of isoschizogamine [J].

Hájícek, J ;

Taimr, J ;

BudÄsínsky, M .

TETRAHEDRON LETTERS, 1998, 39 (5-6) :505-508

[7] A short synthesis of (±)-alloyohimbane via a thioisomunchnone based intramolecular dipolar-cycloaddition reaction [J].

Heidelbaugh, TM ;

Liu, B ;

Padwa, A .

TETRAHEDRON LETTERS, 1998, 39 (27) :4757-4760

[8] REAKTIONEN DES KOHLENSUBOXIDS MIT CARBONYLVERVINDUNGEN [J].

HOPFF, H ;

HEGAR, G .

HELVETICA CHIMICA ACTA, 1961, 44 (07) :2016-&

[9] Total synthesis of (±)-isoschizogamine [J].

Hubbs, JL ;

Heathcock, CH .

ORGANIC LETTERS, 1999, 1 (08) :1315-1317

[10] CARBON SUBOXIDE IN PREPARATIVE ORGANIC-CHEMISTRY [J].

KAPPE, T ;

ZIEGLER, E .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1974, 13 (08) :491-504

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