Preparation of oxepanes, oxepenes, and oxocanes by iodoetherification using bis(sym-collidine)iodine(I) hexafluorophosphate as electrophile

被引：47

作者：

Brunel, Y ^{[1
]}

Rousseau, G ^{[1
]}

机构：

[1] UNIV PARIS 11,INST CHIM MOL ORSAY,LAB CARBOCYCLES,URA CNRS 478,F-91405 ORSAY,FRANCE

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 17期

关键词：

D O I：

10.1021/jo960506t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxepanes have been obtained in good yields (40-95%) by iodoetherification of unsaturated alcohols using bis(sym-collidine)iodine(I) hexafluorophosphate (1) as electrophile, either by 7-exo-mode or 7-endo-mode cyclizations. 4-Oxepenes could also be formed from 4,6-heptadien-1-ols; the presence of a substituent on the carbon 6 appeared necessary, while for steric reasons the presence of a substituent on the carbon 7 was unfavorable. Oxocanes could be obtained in moderate yields (18-27%).

引用

页码：5793 / 5800

页数：8

共 78 条

[61] THERMAL CYCLOADDITIONS OF DIMETHYL ACETYLENEDICARBOXYLATE WITH CYCLIC ENOLETHERS - AN ENTRY INTO MEDIUM SIZE OXOCYCLIC SYSTEMS [J].

NICOLAOU, KC ;

HWANG, CK ;

DUGGAN, ME ;

REDDY, KB .

TETRAHEDRON LETTERS, 1987, 28 (14) :1501-1502

[62] SYNTHETIC STUDIES ON THE DIOXEPANE REGION OF BREVETOXIN-B - NEW SYNTHETIC TECHNOLOGY FOR THE CONSTRUCTION OF OXEPANES AND SYNTHESIS OF A MODEL FOR THE CDEF RING SKELETON OF BREVETOXIN-B [J].

NICOLAOU, KC ;

HWANG, CK ;

NUGIEL, DA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (11) :4136-4137

[63] TOTAL SYNTHESIS OF BREVETOXIN-B .1. FIRST GENERATION STRATEGIES AND NEW APPROACHES TO OXEPANE SYSTEMS [J].

NICOLAOU, KC ;

HWANG, CK ;

DUGGAN, ME ;

NUGIEL, DA ;

ABE, Y ;

REDDY, KB ;

DEFREES, SA ;

REDDY, DR ;

AWARTANI, RA ;

CONLEY, SR ;

RUTJES, FPJT ;

THEODORAKIS, EA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (41) :10227-10238

[64] INTRAMOLECULAR NUCLEOPHILIC-ADDITION TO UNSATURATED CARBON - DEPENDENCE OF CYCLIZATION EFFICIENCY ON THE METHOD OF CARBON CARBON BOND-CLEAVAGE UTILIZED TO GENERATE THE REACTIVE SPECIES [J].

PAQUETTE, LA ;

GILDAY, JP ;

MAYNARD, GD .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (21) :5044-5053

[65] STEREOSPECIFIC APPROACH TO 3-OXOCEN-7-ONES VIA ALIPHATIC CLAISEN REARRANGEMENT - SYNTHESIS OF (+)-(2R,8S)-LAUTHISAN AND (+)-(2R,8R)-LAUTHISAN [J].

PAQUETTE, LA ;

SWEENEY, TJ .

TETRAHEDRON, 1990, 46 (13-14) :4487-4502

[66]

PING G, 1987, B CHIM SOC JPN, V60, P397

[67] RETRACTED: SYNTHESIS OF (+)-LAURENCIN (RETRACTED ARTICLE. SEE VOL 118, PG 6806, 1996) [J].

ROBINSON, RA ;

CLARK, JS ;

HOLMES, AB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10400-10401

[68] MEDIUM RING LACTONES [J].

ROUSSEAU, G .

TETRAHEDRON, 1995, 51 (10) :2777-2849

[69] THE SYNTHESIS OF THE 1ST NATURAL HOST GERMINATION STIMULANT FOR STRIGA-ASIATICA (WITCHWEED) [J].

SARGENT, MV ;

WANGCHAREONTRAKUL, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (05) :1429-1434

[70] CHIRAL, BIOMIMETIC TOTAL SYNTHESIS OF (-)-APLYSISTATIN [J].

SHIEH, HM ;

PRESTWICH, GD .

TETRAHEDRON LETTERS, 1982, 23 (45) :4643-4646

← 1 2 3 4 5 6 7 8 →