A novel and simple method to prepare γ-hydroxy-α,β-(E)-alkenoic esters from γ-keto-alkynoic esters

被引：23

作者：

Naka, T ^{[1
]}

Koide, K ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 03期

关键词：

D O I：

10.1016/S0040-4039(02)02602-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method to convert gamma-keto-alkynoic esters to gamma-hydroxy-alpha,beta-(E)-alkenoic esters is described. This functional group transformation was accomplished in one step by means of NaBH, reduction in methanol. (C) 2002 Elsevier Science Ltd. All rights reserved.

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页码：443 / 445

页数：3

相关论文

共 34 条

[1] CYTOCHALASINS A NEW CLASS OF BIOLOGICALLY ACTIVE MOULD METABOLITES [J].

ALDRIDGE, DC ;

ARMSTRONG, JJ ;

SPEAKE, RN ;

TURNER, WB .

CHEMICAL COMMUNICATIONS, 1967, (01) :26-+

[2] Acremonol and acremodiol, new fungal bislactones [J].

Berg, A ;

Notni, J ;

Dörfelt, H ;

Gräfe, U .

JOURNAL OF ANTIBIOTICS, 2002, 55 (07) :660-662

[3] Synthesis of a complete series of C-4 fluorinated Phe-Gly mimetics [J].

Berts, W ;

Luthman, K .

TETRAHEDRON, 1999, 55 (48) :13819-13830

[4]

BUCHI G, 1973, J AM CHEM SOC, V95, P5423, DOI 10.1021/ja00797a060

[5] OPTICALLY-ACTIVE BUILDING-BLOCKS FROM THE SPAC REACTION - A COMPLETELY ASYMMETRIC-SYNTHESIS OF (4S-CIS)-5-(CYCLOHEXYLMETHYL)-4-HYDROXY-2-PYRROLIDINONE, A STATINE ANALOG [J].

BURGESS, K ;

CASSIDY, J ;

HENDERSON, I .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (06) :2050-2058

[6] NI(II)/CR(II)-MEDIATED COUPLING REACTION - AN ASYMMETRIC PROCESS [J].

CHEN, CP ;

TAGAMI, K ;

KISHI, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (17) :5386-5387

[7] ADDITIVE PUMMERER REACTIONS OF VINYLIC SULFOXIDES - SYNTHESIS OF GAMMA-HYDROXY-ALPHA,BETA-UNSATURATED ESTERS, ALPHA-HYDROXYKETONES, AND 2-PHENYLSULFENYL ALDEHYDES AND PRIMARY ALCOHOLS [J].

CRAIG, D ;

DANIELS, K ;

MACKENZIE, AR .

TETRAHEDRON, 1993, 49 (48) :11263-11304

[8] THE PREPARATION OF ACETYLENIC KETONES USING SOLUBLE SILVER ACETYLIDES [J].

DAVIS, RB ;

SCHEIBER, DH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (08) :1675-1678

[9] HYPOCHOLESTEROLEMIC AGENT COMPACTIN (ML-236B) - TOTAL SYNTHESIS OF THE HEXAHYDRONAPHTHALENE PORTION [J].

FUNK, RL ;

ZELLER, WE .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (01) :180-182

[10] DIASTEREOFACIAL SELECTIVITY IN INTRAMOLECULAR 1,4-CONJUGATE ADDITIONS - CONCLUSIVE EVIDENCE FOR THE IMPORTANCE OF GROUND-STATE CONFORMATIONS AND THE SIGMA(ASTERISK) ORBITAL EFFECT [J].

GUNG, BW ;

FRANCIS, MB .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (23) :6177-6179

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