SYNTHESIS OF MEDIUM-SIZED RING ETHERS FROM THIONOLACTONES - APPLICATIONS TO POLYETHER SYNTHESIS

被引：129

作者：

NICOLAOU, KC ^{[1
]}

MCGARRY, DG ^{[1
]}

SOMERS, PK ^{[1
]}

KIM, BH ^{[1
]}

OGILVIE, WW ^{[1
]}

YIANNIKOUROS, G ^{[1
]}

PRASAD, CVC ^{[1
]}

VEALE, CA ^{[1
]}

HARK, RR ^{[1
]}

机构：

[1] UNIV CALIF SAN DIEGO,DEPT CHEM,LA JOLLA,CA 92093

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1990年 / 112卷 / 17期

关键词：

D O I：

10.1021/ja00173a013

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A variety of medium-sized thionolactones have been prepared and condensed with nucleophiles giving alkylated thioacetals upon quenching with methyl iodide. Reductive desulfurization using triphenyltin hydride under radical conditions afforded the corresponding cyclicethers rapidly and efficiently and, in most cases, with complete stereocontrol. This methodology has been proven through the construction of model systems of rings B and D of brevetoxin A (1) and a synthesis of (±)-lauthisan (44). © 1990, American Chemical Society. All rights reserved.

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页码：6263 / 6276

页数：14

相关论文

共 63 条

[1] SYNTHESIS OF MACROCYCLIC LACTONES - APPROACHES TO COMPLEX MACROLIDE ANTIBIOTICS [J].

BACK, TG .

TETRAHEDRON, 1977, 33 (23) :3041-3059

[2] CONSTRUCTION OF TRANS-FUSED POLYCYCLIC ETHERS - METHODOLOGY FOR THE BREVETOXINS [J].

BARTLETT, PA ;

TING, PC .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (12) :2230-2240

[3] HETEROPHILIC ADDITIONS TO CARBONYLS AND THIOCARBONYLS - SCOPE AND STEREOCHEMISTRY [J].

BEAK, P ;

YAMAMOTO, J ;

UPTON, CJ .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (21) :3052-3062

[4] NEW COPPER CHEMISTRY .9. REACTION OF ORGANOCUPRATES WITH DITHIO ESTERS - DOUBLE-BARRELLED CARBOPHILIC ADDITION AND A NEW SYNTHETIC ROUTE TO TERTIARY THIOLS [J].

BERTZ, SH ;

DABBAGH, G ;

WILLIAMS, M .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (22) :4414-4415

[5] A NEW VINYL ACETYLENE FROM THE RED ALGA LAURENCIA-THYRSIFERA [J].

BLUNT, JW ;

LAKE, RJ ;

MUNRO, MHG ;

YORKE, SC .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1981, 34 (11) :2393-2400

[6] SOLVOMERCURATION-DEMERCURATION .1. OXYMERCURATION-DEMERCURATION OF REPRESENTATIVE OLEFINS IN AN AQUEOUS SYSTEM - A CONVENIENT MILD PROCEDURE FOR MARKOVNIKOV HYDRATION OF CARBON-CARBON DOUBLE BOND [J].

BROWN, HC ;

GEOGHEGA.PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (06) :1844-&

[7] HYDROBORATION .73. RELATIVE RATES OF HYDROBORATION OF REPRESENTATIVE HETEROCYCLIC OLEFINS WITH 9-BORABICYCLO[3.3.1]NONANE [J].

BROWN, HC ;

RAMACHANDRAN, PV ;

PRASAD, JVNV .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5583-5586

[8] SYNTHETIC METHODOLOGY FOR THE PREPARATION OF TRANS-2,9-DISUBSTITUTED AND CIS-2,9-DISUBSTITUTED OXONANES [J].

CARLING, RW ;

CURTIS, NR ;

HOLMES, AB .

TETRAHEDRON LETTERS, 1989, 30 (44) :6081-6084

[9] A NEW SYNTHETIC METHOD FOR THE PREPARATION OF 2,8-DISUBSTITUTED OXOCANE DERIVATIVES - SYNTHESIS OF LAUTHISAN AND LAURENAN [J].

CARLING, RW ;

HOLMES, AB .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (07) :565-567

[10]

CASTANEDA A, 1989, J ORG CHEM, V54, P5707

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