ANNULATIVE RING EXPANSIONS - DIRECT CONVERSION OF OMEGA-ALKYNYL ACETALS TO POLYCYCLIC UNSATURATED-KETONES

被引：20

作者：

SISKO, J ^{[1
]}

BALOG, A ^{[1
]}

CURRAN, DP ^{[1
]}

机构：

[1] UNIV PITTSBURGH,DEPT CHEM,PITTSBURGH,PA 15260

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 16期

关键词：

D O I：

10.1021/jo00042a007

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Geminal acylation of omega-acetylenic acetals and bis(silyloxy)cycloalkenes under Lewis acid conditions preceded cationic cyclization of the alkyne onto the ketone to produce polycyclic unsaturated ketones.

引用

页码：4341 / 4342

页数：2

共 18 条

[1] A USEFUL METHOD FOR PREPARATION OF CARBOXYLIC-ACIDS FROM TERMINAL ALKYNES [J].

ABRAMS, SR .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1983, 61 (10) :2423-2424

[2]

BOERTERPSTRA T, 1977, TETRAHEDRON LETT, P939

[3] 5-6-7-8-TETRAHYDRO-8-METHYLINDANE-1-5-DIONE [J].

BOYCE, CBC ;

WHITEHURST, JS .

JOURNAL OF THE CHEMICAL SOCIETY, 1959, (JUN) :2022-2024

[4]

HARDING CE, 1971, TETRAHEDRON LETT, P1253

[5] MECHANISM OF THE INTRAMOLECULAR CYCLIZATION OF ACETYLENIC KETONES [J].

HARDING, CE ;

KING, SL .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (03) :883-886

[6] MECHANISM OF THE TRANS-ANNULAR CYCLIZATION OF 5-CYCLODECYNONE [J].

HARDING, CE ;

STANFORD, GR .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (13) :3054-3056

[7] RING-ENLARGING CYCLOPENTENE ANNULATIONS [J].

JOHNSON, TO ;

OVERMAN, LE .

TETRAHEDRON LETTERS, 1991, 32 (50) :7361-7364

[8]

JOHNSON WS, 1976, BIOORG CHEM, V5, P51, DOI 10.1016/0045-2068(76)90016-X

[9] FORMATION OF VINYL HALIDES FROM VINYL CATIONS GENERATED BY ACETYLENIC PARTICIPATION IN BIOMIMETIC POLYENE CYCLIZATIONS [J].

JOHNSON, WS ;

WARD, CE ;

BOOTS, SG ;

GRAVESTOCK, MB ;

MARKEZICH, RL ;

MCCARRY, BE ;

OKORIE, DA ;

PARRY, RJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (01) :88-98

[10] NUCLEOPHILE-PROMOTED ELECTROPHILIC CYCLIZATION REACTIONS OF ALKYNES [J].

OVERMAN, LE ;

SHARP, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (02) :612-614

← 1 2 →