BETA-ALKOXYACRYLATES IN RADICAL CYCLIZATIONS - REMARKABLY EFFICIENT OXACYCLE SYNTHESIS

被引：96

作者：

LEE, E

TAE, JS

LEE, C

PARK, CM

机构：

[1] Department of Chemistry, College of Natural Sciences, Seoul National University

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 30期

关键词：

D O I：

10.1016/S0040-4039(00)74101-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Beta-alkoxyacrylates were found to be exceptionally efficient radical acceptors in radical-mediated intramolecular cyclizations. For example, reaction of 5-bromo-2-pentanol with ethyl propiolate, tributylstannane-mediated radical cyclization, and hydrolysis yielded (+/-)-(cis-6-methyltetrahydropyran-2-yl)acetic acid, a known component of civet.

引用

收藏

页码：4831 / 4834

页数：4

相关论文

共 33 条

[1] ROTENOID SYNTHESIS VIA RADICAL CYCLIZATION [J].

AHMADJUNAN, SA ;

WHITING, DA .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (17) :1160-1161

[2]

Bartlett P. A., 1984, ASYMMETRIC SYNTHESIS, V3, P411

[3] REGIO-SELECTIVITY AND STEREO-SELECTIVITY OF ALKENYL RADICAL RING-CLOSURE - A THEORETICAL-STUDY [J].

BECKWITH, ALJ ;

SCHIESSER, CH .

TETRAHEDRON, 1985, 41 (19) :3925-3941

[4] SYNTHETIC ROUTES TO TETRAHYDROFURAN, TETRAHYDROPYRAN, AND SPIROKETAL UNITS OF POLYETHER ANTIBIOTICS AND A SURVEY OF SPIROKETALS OF OTHER NATURAL-PRODUCTS [J].

BOIVIN, TLB .

TETRAHEDRON, 1987, 43 (15) :3309-3362

[5] TETRAHYDROPYRAN SYNTHESIS VIA RADICAL CYCLIZATION - A SYSTEMATIC STUDY OF SUBSTITUENT EFFECTS [J].

BURKE, SD ;

RANCOURT, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (06) :2335-2336

[6] STEREOSELECTIVE SYNTHESIS OF 3-(PHENYLSULFONYL)-2,5-DISUBSTITUTED TETRAHYDROFURANS VIA 5-ENDO-TRIG RING-CLOSURE REACTIONS [J].

CRAIG, D ;

SMITH, AM .

TETRAHEDRON LETTERS, 1992, 33 (05) :695-698

[7]

CURRAN DP, 1988, SYNTHESIS-STUTTGART, V417, P489

[8]

FLEMING I, 1976, FRONTIER ORBITALS OR, P189

[9] STEREOCHEMICAL CONTROL IN REACTIONS OF NUCLEOPHILES WITH OXOCARBENIUM IONS FORMED BY INTRAMOLECULAR OPENING OF ACTIVATED EPOXIDES BY NEIGHBORING CARBONYL GROUPS [J].

FOTSCH, CH ;

CHAMBERLIN, AR .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) :4141-4147

[10]

Giese B., 1986, RADICALS ORGANIC SYN

← 1 2 3 4 →