AN ALTERNATIVE PROCEDURE FOR THE STEREOSELECTIVE FORMATION OF TETRAHYDROPYRAN DERIVATIVES VIA 6-ENDO RING-CLOSURE

被引：45

作者：

MUKAI, C ^{[1
]}

SUGIMOTO, Y ^{[1
]}

IKEDA, Y ^{[1
]}

HANAOKA, M ^{[1
]}

机构：

[1] KANAZAWA UNIV,FAC PHARMACEUT SCI,KANAZAWA 920,JAPAN

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 14期

关键词：

D O I：

10.1016/S0040-4039(00)76791-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of the acetylenic epoxides I having electron-donating groups at the acetylenic terminus with a catalytic amount of BF3.OEt(2) afforded 6-endo products with inversion of stereochemistry at the propynyl position in a highly stereoselective manner, whereas the acetylenic epoxides I possessing electron-withdrawing substitutents at the acetylenic terminus provided under similar acidic condition the corresponding tetrahydrofuran derivatives in a highly selective way.

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页码：2183 / 2186

页数：4

相关论文

共 11 条

[1] STEREOCHEMICAL ASPECTS OF CYTOSOLIC EPOXIDE HYDROLASE HYDRATION OF METHYL DIEPOXYSTEARATES [J].

BORHAN, B ;

NOUROOZZADEH, J ;

UEMATSU, T ;

HAMMOCK, BD ;

KURTH, MJ .

TETRAHEDRON, 1993, 49 (13) :2601-2612

[2] GENERAL-APPROACH TO HALOGENATED TETRAHYDROFURAN NATURAL-PRODUCTS FROM RED ALGAE OF THE GENUS LAURENCIA - TOTAL SYNTHESIS OF (+/-)-KUMAUSALLENE AND (+/-)-1-EPI-KUMAUSALLENE [J].

GRESE, TA ;

HUTCHINSON, KD ;

OVERMAN, LE .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (09) :2468-2477

[3]

KARAKHANOV RA, 1983, KHIM GETEROTSIKL+, P1602

[4] REGIOSELECTIVE AND STEREOSPECIFIC FORMATION OF 2-ETHYNYL-3-HYDROXYTETRAHYDROPYRAN DERIVATIVES VIA 6-ENDO RING-CLOSURE [J].

MUKAI, C ;

IKEDA, Y ;

SUGIMOTO, Y ;

HANAOKA, M .

TETRAHEDRON LETTERS, 1994, 35 (14) :2179-2182

[5] ACTIVATION OF 6-ENDO OVER 5-EXO EPOXIDE OPENINGS - RING-SELECTIVE FORMATION OF TETRAHYDROPYRAN SYSTEMS AND STEREOCONTROLLED SYNTHESIS OF THE ABC RING FRAMEWORK OF BREVETOXIN-B [J].

NICOLAOU, KC ;

DUGGAN, ME ;

HWANG, CK ;

SOMERS, PK .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (19) :1359-1362

[6] ACTIVATION OF 7-ENDO OVER 6-EXO EPOXIDE OPENINGS - SYNTHESIS OF OXEPANE AND TETRAHYDROPYRAN SYSTEMS [J].

NICOLAOU, KC ;

PRASAD, CVC ;

SOMERS, PK ;

HWANG, CK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) :5335-5340

[7] ACTIVATION OF 6-ENDO OVER 5-EXO HYDROXY EPOXIDE OPENINGS - STEREOSELECTIVE AND RING SELECTIVE SYNTHESIS OF TETRAHYDROFURAN AND TETRAHYDROPYRAN SYSTEMS [J].

NICOLAOU, KC ;

PRASAD, CVC ;

SOMERS, PK ;

HWANG, CK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) :5330-5334

[8] CYCLIZATIONS OF HYDROXY DITHIOKETALS - NEW SYNTHETIC TECHNOLOGY FOR THE CONSTRUCTION OF OXOCENES AND RELATED MEDIUM-RING SYSTEMS [J].

NICOLAOU, KC ;

PRASAD, CVC ;

HWANG, CK ;

DUGGAN, ME ;

VEALE, CA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) :5321-5330

[9] A GENERAL-APPROACH TO GAMMA-LACTONES VIA OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION - SYNTHESIS OF (-)-MURICATACIN AND (+)-MURICATACIN [J].

WANG, ZM ;

ZHANG, XL ;

SHARPLESS, KB ;

SINHA, SC ;

SINHABAGCHI, A ;

KEINAN, E .

TETRAHEDRON LETTERS, 1992, 33 (43) :6407-6410

[10] LATERAL ROOT INDUCING COMPOUNDS FROM THE BACTERIUM ERWINIA-QUERCINA - ISOLATION, STRUCTURE AND SYNTHESIS [J].

WRIGHT, AE ;

SCHAFER, M ;

MIDLAND, S ;

MUNNECKE, DE ;

SIMS, JJ .

TETRAHEDRON LETTERS, 1989, 30 (42) :5699-5702