An efficient and simple synthesis of (-)-wine lactone

被引：14

作者：

Chavan, SP ^{[1
]}

Kharul, RK ^{[1
]}

Sharma, AK ^{[1
]}

Chavan, SP ^{[1
]}

机构：

[1] Natl Chem Lab, Div Organ Chem Technol, Pune 411008, Maharashtra, India

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 21期

关键词：

D O I：

10.1016/S0957-4166(01)00511-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A, short and efficient diastereoselective synthesis of (-)-wine lactone (-)-4a involving FeCl3/NaI-mediated iodolactonization of gamma,delta-unsaturated acid 7 as the key stop is described. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：2985 / 2988

页数：4

共 24 条

[1] EVALUATION OF THE CLAISEN REARRANGEMENT OF 2-CYCLOHEXENOLS FOR THE STEREOSELECTIVE CONSTRUCTION OF A TERPENE SYNTHON [J].

BARTLETT, PA ;

PIZZO, CF .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3896-3900

[2] STEREOSELECTIVE EPOXIDATION OF ACYCLIC OLEFINIC CARBOXYLIC-ACIDS VIA IODO-LACTONIZATION [J].

BARTLETT, PA ;

MYERSON, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (12) :3950-3952

[3] CHIRAL SYNTHONS FOR THE ELABORATION OF MEVINIC ACID ANALOGS [J].

BENNETT, F ;

KNIGHT, DW ;

FENTON, G .

TETRAHEDRON LETTERS, 1988, 29 (38) :4865-4868

[4]

Bergner EJ, 2000, EUR J ORG CHEM, V2000, P419, DOI 10.1002/(SICI)1099-0690(200002)2000:3<419::AID-EJOC419>3.0.CO

[5]

2-N

[6] Isolation of two novel terpenoid glucose esters from Riesling wine [J].

Bonnländer, B ;

Baderschneider, B ;

Messerer, M ;

Winterhalter, P .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1998, 46 (04) :1474-1478

[7] RESEARCHES ON ACETYLENIC COMPOUNDS .1. THE PREPARATION OF ACETYLENIC KETONES BY OXIDATION OF ACETYLENIC CARBINOLS AND GLYCOLS [J].

BOWDEN, K ;

HEILBRON, IM ;

JONES, ERH ;

WEEDON, BCL .

JOURNAL OF THE CHEMICAL SOCIETY, 1946, (JAN) :39-45

[8]

Brown H.C, 1975, ORGANIC SYNTHESIS VI

[9] STEREOSELECTIVE IODOLACTONIZATION OF ACYCLIC UNSATURATED 3-HYDROXYACIDS [J].

CHAMBERLIN, AR ;

DEZUBE, M ;

DUSSAULT, P .

TETRAHEDRON LETTERS, 1981, 22 (46) :4611-4614

[10] Iodolactonization and iodoetherification of β,γ-unsaturated acids and alcohols using FeCl3 and NaI [J].

Chavan, SP ;

Sharma, AK .

TETRAHEDRON LETTERS, 2001, 42 (29) :4923-4924

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