Practical synthesis of (±)-chlorovulone II

被引：32

作者：

Ciufolini, MA ^{[1
]}

Zhu, SR ^{[1
]}

机构：

[1] Rice Univ, Dept Chem, Houston, TX 77005 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 05期

关键词：

D O I：

10.1021/jo972073f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe a total synthesis of (+/-)-chlorovulone II that is 10 steps shorter than the best alternative currently available (nine vs 19 steps). The key event of the synthesis is an aldol addition of the enolate of ethyl acetate into 4-cyclopentene-1,3-dione, a substance that has received little attention as an educt for prostanoid synthesis and for which little is known about carbonyl 1,2-addition with enolates. In addition, we provide chemical and stereochemical details of a route to a key intermediate toward the title compound that involves a carbonyl-ene reaction and a radical addition to an aldehyde carbonyl.

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页码：1668 / 1675

页数：8

相关论文

共 64 条

[1] STEREOCHEMISTRY OF THE REVERSIBLE CYCLIZATION OF OMEGA-FORMYLALKYL RADICALS [J].

BECKWITH, ALJ ;

RANER, KD .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (18) :4954-4962

[2] FORMATION OF AN ALLENE OXIDE FROM (8R)-8-HYDROPEROXYEICOSATETRAENOIC ACID IN THE CORAL PLEXAURA-HOMOMALLA [J].

BRASH, AR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (05) :1891-1892

[3] ISOLATION AND CHARACTERIZATION OF NATURAL ALLENE OXIDES - UNSTABLE INTERMEDIATES IN THE METABOLISM OF LIPID HYDROPEROXIDES [J].

BRASH, AR ;

BAERTSCHI, SW ;

INGRAM, CD ;

HARRIS, TM .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1988, 85 (10) :3382-3386

[4]

CARDINALE G, 1987, RECL TRAV CHIM PAY B, V106, P62

[5] CATALYTIC, ENANTIOSELECTIVE ACETONE ALDOL ADDITIONS WITH 2-METHOXYPROPENE [J].

CARREIRA, EM ;

LEE, W ;

SINGER, RA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (12) :3649-3650

[6]

CIUFOLINI MA, 1997, IN PRESS TETRAHEDRON, V38

[7]

Claus R. E., 1990, ORG SYNTH COLL, V7, P168

[8] INTERMEDIACY OF 8-(R)-HPETE IN THE CONVERSION OF ARACHIDONIC-ACID TO PRE-CLAVULONE-A BY CLAVULARIA-VIRIDIS - IMPLICATIONS FOR THE BIOSYNTHESIS OF MARINE PROSTANOIDS [J].

COREY, EJ ;

DALARCAO, M ;

MATSUDA, SPT ;

LANSBURY, PT ;

YAMADA, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (01) :289-290

[9] GENERALITY OF MARINE PROSTANOID BIOSYNTHESIS BY THE 2-OXIDOPENTADIENYL CATION PATHWAY [J].

COREY, EJ ;

MATSUDA, SPT .

TETRAHEDRON LETTERS, 1987, 28 (37) :4247-4250

[10] TOTAL SYNTHESIS OF (+/-)-CLAVULONES [J].

COREY, EJ ;

MEHROTRA, MM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (11) :3384-3384

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