A bicyclo[3.2.0]hept-3-en-6-one approach to prostaglandin intermediates

被引：20

作者：

Marotta, E ^{[1
]}

Righi, P ^{[1
]}

Rosini, G ^{[1
]}

机构：

[1] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 26期

关键词：

D O I：

10.1021/ol006664v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The substituted cyclopentanic structures, 6-benzyloxymethyl-7-hydroxy-2-oxabicyclo (1), a Corey lactone derivative, and 6-exo-benzyloxymethyl-2-oxabicyclo[3.3.0]oct-7-en-3-one (2), have been obtained stereoselectively through the bicyclo[3.2.0]hept-3-en-6-one approach via 5-benzyloxymethyl-3-hydroxy-6-heptenoic acid, easily accessible from the inexpensive monoprotected cis-2-butene-1,4-diol.

引用

收藏

页码：4145 / 4148

页数：4

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共 75 条

[11]

COREY EJ, 1972, TETRAHEDRON LETT, P107

[12] STEREO-CONTROLLED SYNTHESIS OF PROSTAGLANDINS F2ALPHA AND E2 (DL) [J].

COREY, EJ ;

WEINSHENKER, NM ;

SCHAAF, TK ;

HUBER, W .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (20) :5675-+

[13] CATALYTIC ENANTIOSELECTIVE SYNTHESIS OF A KEY INTERMEDIATE FOR THE SYNTHESIS OF PROSTANOIDS [J].

COREY, EJ ;

IMAI, N ;

PIKUL, S .

TETRAHEDRON LETTERS, 1991, 32 (51) :7517-7520

[14] PREPARATION OF AN OPTICALLY-ACTIVE INTERMEDIATE FOR SYNTHESIS OF PROSTAGLANDINS [J].

COREY, EJ ;

SNIDER, BB .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (02) :256-258

[15]

CRABBE P, 1972, TETRAHEDRON LETT, P115

[16] A versatile and highly selective hypervalent iodine (III)/2,2,6,6-tetramethyl-1-piperidinyloxyl-mediated oxidation of alcohols to carbonyl compounds [J].

DeMico, A ;

Margarita, R ;

Parlanti, L ;

Vescovi, A ;

Piancatelli, G .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) :6974-6977

[17] A DIRECT ALCOHOL FOR HYDRAZINE INTERCHANGE - SCOPE AND STEREOCHEMISTRY [J].

DOW, RL ;

KELLY, RC ;

SCHLETTER, I ;

WIERENGA, W .

SYNTHETIC COMMUNICATIONS, 1981, 11 (01) :43-53

[18] Asymmetric [3.3]-sigmatropic rearrangements in organic synthesis [J].

Enders, D ;

Knopp, M ;

Schiffers, R .

TETRAHEDRON-ASYMMETRY, 1996, 7 (07) :1847-1882

[19]

Erdik E, 1996, ORGANOZINC REAGENTS

[20] Microbial reduction of methyl-substituted bicyclo[3.2.0]hept-3-en-6-ones: A screening to homochiral endo- and exo-alcohols [J].

Fantin, G ;

Fogagnolo, M ;

Medici, A ;

Pedrini, P ;

Marotta, E ;

Monti, M ;

Righi, P .

TETRAHEDRON-ASYMMETRY, 1996, 7 (01) :277-282

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