Simple and efficient synthesis of thysanone methyl ether

被引：17

作者：

Bulbule, Vivek J.

Koranne, Priti S.

Deshpande, Vishnu H.

Borate, Hanumant B.

机构：

[1] Kochi Univ, Fac Sci, Kochi 7808520, Japan

[2] Natl Chem Lab, Div Organ Chem Technol, Pune 411008, Maharashtra, India

来源：

TETRAHEDRON | 2007年 / 63卷 / 01期

基金：

日本学术振兴会;

关键词：

Michael addition; orsellinate derivative; semivioxanthin; human pathogen;

D O I：

10.1016/j.tet.2006.10.038

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of thysanone methyl ether is achieved by employing semivioxanthin methyl ether, which in turn is prepared by the tandem Michael addition of an anion of orsellinate to a substituted dihydropyrone. (c) 2006 Elsevier Ltd. All rights reserved.

引用

收藏

页码：166 / 170

页数：5

相关论文

共 28 条

[1] FLEXIBLE NEW SYNTHETIC ROUTE TO DAUNOMYCINONE, ADRIAMYCINONE, AND THEIR 6-DEOXY ANALOGS [J].

BOECKMAN, RK ;

CHEON, SH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (12) :4112-4113

[2] Stereoselective synthesis of deoxy analogues of the 3C-protease inhibitor thysanone [J].

Brimble, MA ;

Elliott, RJR .

TETRAHEDRON, 2002, 58 (01) :183-189

[3] PSORALENE .2. CERTAIN REACTIONS OF XANTHOTOXIN [J].

BROKKE, ME ;

CHRISTENSEN, BE .

JOURNAL OF ORGANIC CHEMISTRY, 1959, 24 (04) :523-526

[4] Simple synthesis of two naphthoquinone antibiotics psychorubrin and pentalongin [J].

Bulbule, VJ ;

Koranne, PS ;

Munot, YS ;

Borate, HB ;

Deshpande, VH .

SYNTHETIC COMMUNICATIONS, 2003, 33 (04) :587-594

[5] CLEAVAGE OF SMALL PEPTIDES INVITRO BY HUMAN RHINOVIRUS 14-3C PROTEASE EXPRESSED IN ESCHERICHIA-COLI [J].

CORDINGLEY, MG ;

REGISTER, RB ;

CALLAHAN, PL ;

GARSKY, VM ;

COLONNO, RJ .

JOURNAL OF VIROLOGY, 1989, 63 (12) :5037-5045

[6]

CORDINGLEY MG, 1990, J BIOL CHEM, V265, P9062

[7]

DEAN FM, 1966, TETRAHEDRON LETT, P4153

[8] Simple Syntheses of (+)-orthosporin and (-)-semivioxanthin methyl ether [J].

Deshpande, VH ;

Rai, B ;

Khan, RA .

TETRAHEDRON, 1996, 52 (20) :7159-7162

[9] SYNTHESIS OF SEMIVIOXANTHIN [J].

DESHPANDE, VH ;

KHAN, RA ;

RAI, B ;

AYYANGAR, NR .

SYNTHETIC COMMUNICATIONS, 1993, 23 (17) :2337-2345

[10] Pigments of fungi. Part 68. Synthesis and absolute configuration of thysanone [J].

Donner, CD ;

Gill, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (07) :938-948