A NEW APPROACH TO FUNCTIONALIZED CYCLOBUTANES - STEREOSELECTIVE SYNTHESIS OF THE ENANTIOMERS OF GRANDISOL AND FRAGANOL

被引：33

作者：

MARTIN, T ^{[1
]}

RODRIGUEZ, CM ^{[1
]}

MARTIN, VS ^{[1
]}

机构：

[1] UNIV LA LAGUNA,INST BIOORGAN,CTR PROD NAT ORGAN ANTONIO GONZALEZ,E-38206 LA LAGUNA,SPAIN

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 05期

关键词：

D O I：

10.1016/0957-4166(95)00141-B

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Enantiomerically enriched (+)-grandisol and (+)-fraganol were synthesized using as the key step a new stereoselective synthesis of cyclobutanes fused to gamma-lactones by a stereochemically-controlled intramolecular alkylation of alpha-benzenesulfonyl-gamma-lactones. This method provides a way to synthesize the enantiomers in a straightforward manner.

引用

页码：1151 / 1164

页数：14

共 18 条

[1] DIASTEREOSELECTIVE AND HIGHLY EFFICIENT RADICAL APPROACH TO (1S,6R) AND (1R,6S)-2,2,6-TRIMETHYL-3-OXABICYCLO[4.2.0]OCTADECANE, KEY INTERMEDIATES IN THE SYNTHESIS OF (+)-GRANDISOL AND (-)-GRANDISOL [J].

ALIBES, R ;

BOURDELANDE, JL ;

FONT, J .

TETRAHEDRON LETTERS, 1994, 35 (16) :2587-2588

[2] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[3]

Djerassi C., 1994, DICT NATURAL PRODUCT, V3, P2984

[4]

EVANS DA, 1988, J AM CHEM SOC, V110, P2501

[5] CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION [J].

GAO, Y ;

HANSON, RM ;

KLUNDER, JM ;

KO, SY ;

MASAMUNE, H ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) :5765-5780

[6]

KATSUKI T, 1980, J AM CHEM SOC, V102, P5976

[7]

KATZENELLENBOGE.JA, 1976, SCIENCE, V194, P139

[8] A STEREOSPECIFIC SYNTHESIS OF (+/-)-GRANDISOL VIA AN INTRAMOLECULAR LACTONE ENOLATE ALKYLATION - A REMARKABLE REGIODIVERGENCE IN C-ALKYLATION VS O-ALKYLATION [J].

KIM, D ;

KWAK, YS ;

SHIN, KJ .

TETRAHEDRON LETTERS, 1994, 35 (49) :9211-9212

[9] KINETIC RESOLUTION OF RACEMIC ALLYLIC ALCOHOLS BY ENANTIOSELECTIVE EPOXIDATION - A ROUTE TO SUBSTANCES OF ABSOLUTE ENANTIOMERIC PURITY [J].

MARTIN, VS ;

WOODARD, SS ;

KATSUKI, T ;

YAMADA, Y ;

IKEDA, M ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (20) :6237-6240

[10]

MORI K, 1992, LIEBIGS ANN CHEM, P489

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