A SYNTHETIC APPROACH TOWARDS OCTALACTIN-A, BASED ON THE STEREOSELECTIVE REDUCTION OF ALPHA,BETA-UNSATURATED KETONES

被引：41

作者：

BACH, J ^{[1
]}

BERENGUER, R ^{[1
]}

GARCIA, J ^{[1
]}

VILARRASA, J ^{[1
]}

机构：

[1] UNIV BARCELONA,DEPT QUIM ORGAN,DIV 3,E-08028 BARCELONA,SPAIN

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 19期

关键词：

D O I：

10.1016/0040-4039(95)00498-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient enantioselective synthesis of the C3-C9 fragment of Octalactin A and studies aimed at the conversion of Octalactin B into Octalactin A are described, which are based on the borane-mediated reduction of alpha,beta-unsaturated ketones catalysed by B-methyl-4,5,5-triphenyl-1,3,2-oxazaborolidines (9). A comparative study of the reduction of 2-methylnon-1-en-3-one (10) -a model of the Octalactin-A C3-C9 moiety- with different chiral reagents has also been performed.

引用

页码：3425 / 3428

页数：4

共 19 条

[1] ENANTIOSELECTIVE REDUCTION OF ACETOPHENONE WITH 1,3,2-OXAZABOROLIDINES DERIVED FROM EPHEDRINE, PSEUDOEPHEDRINE, AND PHENYLGLYCINE [J].

BERENGUER, R ;

GARCIA, J ;

GONZALEZ, M ;

VILARRASA, J .

TETRAHEDRON-ASYMMETRY, 1993, 4 (01) :13-16

[2] ENANTIOSELECTIVE REDUCTION OF KETONES CATALYZED BY 1,3,2-OXAZABOROLIDINES PREPARED FROM PHENYLGLYCINE [J].

BERENGUER, R ;

GARCIA, J ;

VILARRASA, J .

TETRAHEDRON-ASYMMETRY, 1994, 5 (02) :165-168

[3] TRANSITION-METAL-PROMOTED HYDROBORATIONS OF ALKENES, EMERGING METHODOLOGY FOR ORGANIC TRANSFORMATIONS [J].

BURGESS, K ;

OHLMEYER, MJ .

CHEMICAL REVIEWS, 1991, 91 (06) :1179-1191

[4] TOTAL SYNTHESIS OF OCTALACTIN-A AND OCTALACTIN-B [J].

BUSZEK, KR ;

SATO, N ;

JEONG, YM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (12) :5511-5512

[5] AN EFFICIENT AND CATALYTICALLY ENANTIOSELECTIVE ROUTE TO (S)-(-)-PHENYLOXIRANE [J].

COREY, EJ ;

SHIBATA, S ;

BAKSHI, RK .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (12) :2861-2863

[6] SELECTIVE OXIDATION OF ALDEHYDES TO CARBOXYLIC-ACIDS WITH SODIUM-CHLORITE HYDROGEN-PEROXIDE [J].

DALCANALE, E ;

MONTANARI, F .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04) :567-569

[7] RHODIUM(I)-CATALYZED HYDROBORATION OF OLEFINS - THE DOCUMENTATION OF REGIOCHEMICAL AND STEREOCHEMICAL CONTROL IN CYCLIC AND ACYCLIC SYSTEMS [J].

EVANS, DA ;

FU, GC ;

HOVEYDA, AH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) :6917-6918

[8] ENANTIOSELECTIVE MICHAEL REACTIONS - DIASTEREOSELECTIVE REACTIONS OF CHLOROTITANIUM ENOLATES OF CHIRAL N-ACYLOXAZOLIDINONES WITH REPRESENTATIVE ELECTROPHILIC OLEFINS [J].

EVANS, DA ;

BILODEAU, MT ;

SOMERS, TC ;

CLARDY, J ;

CHERRY, D ;

KATO, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5750-5752

[9] TOTAL SYNTHESIS OF (+)-CALYCULIN-A [J].

EVANS, DA ;

GAGE, JR ;

LEIGHTON, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) :9434-9453

[10] ASYMMETRIC REDUCTION OF PROCHIRAL CYCLIC-KETONES WITH LITHIUM ALUMINUM-HYDRIDE PARTIALLY DECOMPOSED BY (1R,2S)-(-)-N-METHYLEPHEDRINE AND 2-ALKYLAMINOPYRIDINE [J].

KAWASAKI, M ;

SUZUKI, Y ;

TERASHIMA, S .

CHEMISTRY LETTERS, 1984, (02) :239-242

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