A brief synthesis of the Aplasmomycin tetrahydrofuran

被引：17

作者：

Bew, SP ^{[1
]}

Knight, DW ^{[1
]}

Middleton, RJ ^{[1
]}

机构：

[1] Cardiff Univ, Dept Chem, Cardiff CF10 3TB, S Glam, Wales

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 22期

基金：

英国工程与自然科学研究理事会;

关键词：

aplasmomycin; 5-endo; iodocyclisation; asymmetric; tetrahydrofuran;

D O I：

10.1016/S0040-4039(00)00614-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly stereoselective iodocyclisation of the 3-alkene-1,2-diol 9, derived from asymmetric dihydroxylation of the dienyl benzoate 8, gives the beta-iodotetrahydrofuran 10 and thence the Aplasmomycin precursor 13, following deiodination and Mitsunobu inversion. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：4453 / 4456

页数：4

共 26 条

[1]

ALAMI M, 1993, SYNLETT, P217

[2] SELECTIVE ASYMMETRIC DIHYDROXYLATION OF POLYENES [J].

BECKER, H ;

SOLER, MA ;

SHARPLESS, KB .

TETRAHEDRON, 1995, 51 (05) :1345-1376

[3] Total synthesis of tartrolon B [J].

Berger, M ;

Mulzer, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (36) :8393-8394

[4] Stereochemical features of iodocyclisations of 3-alkene-1,2-diols to β-hydroxytetrahydrofurans [J].

Bew, SP ;

Barks, JM ;

Knight, DW ;

Middleton, RJ .

TETRAHEDRON LETTERS, 2000, 41 (22) :4447-4451

[5] TOTAL SYNTHESIS OF APLASMOMYCIN - STEREOCONTROLLED CONSTRUCTION OF THE C(3)-C(17) FRAGMENT [J].

COREY, EJ ;

PAN, BC ;

HUA, DH ;

DEARDORFF, DR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (24) :6816-6818

[6]

COREY EJ, 1982, J AM CHEM SOC, V104, P6818, DOI 10.1021/ja00388a074

[7] EFFECT OF THE ACIDIC COMPONENT ON THE MITSUNOBU INVERSION OF A STERICALLY HINDERED ALCOHOL [J].

DODGE, JA ;

TRUJILLO, JI ;

PRESNELL, M .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (01) :234-236

[8] CHEMICAL STUDIES OF MARINE-BACTERIA - DEVELOPING A NEW RESOURCE [J].

FENICAL, W .

CHEMICAL REVIEWS, 1993, 93 (05) :1673-1683

[9] TOTAL SYNTHESIS OF THE C-3-C-17 SEGMENT OF BOROMYCIN [J].

HANESSIAN, S ;

DELORME, D ;

TYLER, PC ;

DEMAILLY, G ;

CHAPLEUR, Y .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1983, 61 (03) :634-637

[10] STRUCTURE AND BIOSYNTHESIS OF BOROPHYCIN, A NEW BOESEKEN COMPLEX OF BORIC-ACID FROM A MARINE STRAIN OF THE BLUE-GREEN-ALGA NOSTOC LINCKIA [J].

HEMSCHEIDT, T ;

PUGLISI, MP ;

LARSEN, LK ;

PATTERSON, GML ;

MOORE, RE ;

RIOS, JL ;

CLARDY, J .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3467-3471

← 1 2 3 →