A new synthetic approach for 4(S)-hydroxycyclopent-2-enone:: a precursor to prostanoid synthesis

被引：7

作者：

Chang, CT

Jacobo, SH

Powell, WS

Lawson, JA

Fitzgerald, GA

Pratico, D

Rokach, J

机构：

[1] Florida Inst Technol, Claude Pepper Inst, Melbourne, FL 32901 USA

[2] Florida Inst Technol, Dept Chem, Melbourne, FL 32901 USA

[3] McGill Univ, Meakins Christie Labs, Dept Med, Montreal, PQ H2X 2P2, Canada

[4] Univ Penn, Inst Translata Med & Therapeut, Philadelphia, PA 19104 USA

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 37期

基金：

美国国家科学基金会; 加拿大健康研究院; 美国国家卫生研究院;

关键词：

4(S)-hydroxycyclopent-2-enone; olefin metathesis; synthesis;

D O I：

10.1016/j.tetlet.2005.07.035

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new and efficient approach to 4(S)-hydroxycyclopent-2-enone is presented. This methodology allows the preparation of 4(S)-hydroxycyclopent-2-enone in large scale and with high optical purity. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：6325 / 6328

页数：4

共 35 条

[1] SYNTHESIS OF LIPOXINS - TOTAL SYNTHESIS OF CONJUGATED TRIHYDROXY EICOSATETRAENOIC ACIDS [J].

ADAMS, J ;

FITZSIMMONS, BJ ;

ROKACH, J .

TETRAHEDRON LETTERS, 1984, 25 (42) :4713-4716

[2]

Armstrong S. K. J., 1998, J CHEM SOC P1, V2, P371

[3] A NOVEL ASYMMETRIC-SYNTHESIS OF CHIRAL CYCLOPENTANOID BUILDING-BLOCKS BY THE USE OF CHIRAL LITHIUM AMIDE [J].

ASAMI, M .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (05) :1402-1408

[4] SYNTHESIS OF VERSATILE INTERMEDIATES FOR CYCLOPENTANOID NATURAL-PRODUCTS VIA ENANTIOSELECTIVE DEPROTONATION OF SUBSTITUTED CYCLOPENTENE OXIDE [J].

BHUNIYA, D ;

GUPTA, AD ;

SINGH, VK .

TETRAHEDRON LETTERS, 1995, 36 (16) :2847-2850

[5] A new and efficient chemoenzymatic access to both enantiomers of 4-hydroxycyclopent-2-en-1-one [J].

Demir, AS ;

Sesenoglu, O .

TETRAHEDRON-ASYMMETRY, 2002, 13 (06) :667-670

[6] TOTAL SYNTHESES OF (+)-DIDEMNENONE-A AND (-)-DIDEMNENONE-A AND (+)-DIDEMNENONE-B AND (-)-DIDEMNENONE-B - ANTISELECTIVITY IN THE INTRAMOLECULAR CARBOMERCURATION REACTION [J].

FORSYTH, CJ ;

CLARDY, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (09) :3497-3505

[7] Enzymatic kinetic resolution studies of racemic 4-hydroxycyclopent-2-en-1-one using Lipozyme IM® [J].

Ghorpade, SR ;

Bastawade, KB ;

Gokhale, DV ;

Shinde, PD ;

Mahajan, VA ;

Kalkote, UR ;

Ravindranathan, T .

TETRAHEDRON-ASYMMETRY, 1999, 10 (21) :4115-4122

[8]

GILL M, 1979, TETRAHEDRON LETT, V20, P1539

[9] Recent advances in olefin metathesis and its application in organic synthesis [J].

Grubbs, RH ;

Chang, S .

TETRAHEDRON, 1998, 54 (18) :4413-4450

[10] STUDIES RELATED TO CYCLOPENTANOID NATURAL-PRODUCTS .3. SYNTHESIS OF PENTENOMYCIN AND ITS RACEMATE [J].

HETMANSKI, M ;

PURCELL, N ;

STOODLEY, RJ ;

PALFREYMAN, MN .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (09) :2089-2096

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