A concise and efficient synthesis of (-)-allosamizoline

被引：25

作者：

Donohoe, Timothy J. ^{[1
]}

Rosa, Carla P. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 26期

关键词：

D O I：

10.1021/ol702449m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A regio- and stereocontrolled total synthesis of (-)-allosamizoline is described. The key steps for this synthesis are ring-closing metathesis to form the cyclopentene core, halocyclization to afford the oxazoline ring, and finally stereoselective alkene radical addition followed by an alkene isomerization reaction to install the hydroxymethyl group. (-)-Allosamizoline was prepared in a total of 13 steps and 22% overall yield.

引用

页码：5509 / 5511

页数：3

共 35 条

[1] BIOCHEMISTRY OF INSECT CUTICLE [J].

ANDERSEN, SO .

ANNUAL REVIEW OF ENTOMOLOGY, 1979, 24 :29-61

[2] Selective isomerization of a terminal olefin catalyzed by a ruthenium complex: The synthesis of indoles through ring-closing metathesis [J].

Arisawa, M ;

Terada, Y ;

Nakagawa, M ;

Nishida, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (24) :4732-4734

[3] Development of isomerization and cycloisomerization with use of a ruthenium hydride with N-heterocyclic carbene and its application to the synthesis of heterocycles [J].

Arisawa, Mitsuhiro ;

Terada, Yukiyoshi ;

Takahashi, Kazuyuki ;

Nakagawa, Masako ;

Nishida, Atsushi .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (11) :4255-4261

[4] SYNTHESIS OF N,N'-DISUBSTITUTED UREAS FROM CARBAMATES [J].

BASHA, A .

TETRAHEDRON LETTERS, 1988, 29 (21) :2525-2526

[5] Synthesis and biological activity of natural aminocyclopentitol glycosidase inhibitors: Mannostatins, trehazolin, allosamidins, and their analogues [J].

Berecibar, A ;

Grandjean, C ;

Siriwardena, A .

CHEMICAL REVIEWS, 1999, 99 (03) :779-844

[6] CARBOCYCLIC COMPOUNDS FROM MONOSACCHARIDES .1. TRANSFORMATIONS IN THE GLUCOSE SERIES [J].

BERNET, B ;

VASELLA, A .

HELVETICA CHIMICA ACTA, 1979, 62 (06) :1990-2016

[7] SYNTHESES OF THE FUNGICIDE/INSECTICIDE ALLOSAMIDIN AND A STRUCTURAL ISOMER [J].

BLATTNER, R ;

FURNEAUX, RH ;

KEMMITT, T ;

TYLER, PC ;

FERRIER, RJ ;

TIDEN, AK .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (23) :3411-3421

[8]

CABIB E, 1981, BIOL CARBOHYDRATES, V1, P60

[9] Total synthesis of both methyl 4a-carba-D-arabinofuranosides [J].

Callam, CS ;

Lowary, TL .

ORGANIC LETTERS, 2000, 2 (02) :167-169

[10] TOTAL SYNTHESIS OF (+/-)-ALLOSAMIZOLINE FROM A SYMMETRICAL TRISUBSTITUTED CYCLOPENTENE [J].

GOERING, BK ;

GANEM, B .

TETRAHEDRON LETTERS, 1994, 35 (38) :6997-7000

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