Investigations towards the synthesis of xylindein, a blue-green pigment from the fungus Chlorociboria aeruginosa

被引：22

作者：

Donner, Christopher D. ^{[1
,2
]}

Cuzzupe, Anthony N. ^{[1
]}

Falzon, Cheryl L. ^{[1
]}

Gill, Melvyn ^{[1
]}

机构：

[1] Univ Melbourne, Sch Chem, Melbourne, Vic 3010, Australia

[2] Univ Melbourne, Mol Sci & Biotechnol Inst Bio21, Melbourne, Vic 3010, Australia

来源：

TETRAHEDRON | 2012年 / 68卷 / 13期

关键词：

Xylindein; Extended quinone; Diets-Alder; Fungal pigment; ABSOLUTE-CONFIGURATION; KETENE ACETALS; NAPHTHOPYRANONE; ANTHRAQUINONES; MODEL; WOOD;

D O I：

10.1016/j.tet.2012.02.009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An approach towards the synthesis of the fungal pigment xylindein 1 is described. Synthesis of the pyranonaphthoquinone corresponding to one half of the xylindein framework is achieved over 11 steps from 1,2-epoxypentane, utilizing multiple Diets Alder cycloaddition processes. Methods for self-coupling of dihydroxynaphthoquinones to give extended quinones are explored. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.

引用

页码：2799 / 2805

页数：7

共 22 条

[1] REGIOSELECTIVE O-DEMETHYLATION IN APORPHINE ALKALOID SERIES [J].

AHMAD, R ;

SAA, JM ;

CAVA, MP .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (07) :1228-1230

[2] REACTIONS OF KETENE ACETALS .8. SIMPLE SYNTHESES OF METHYL ESTER ETHERS OF ANTHRAQUINONES ENDOCROCIN, PTILOMETRIC ACID, AND CLAVORUBIN [J].

BANVILLE, J ;

BRASSARD, P .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (18) :3018-3020

[3]

BLACKBUR.GM, 1965, CHIMIA, V19, P208

[4]

BLACKBURN GM, 1962, P CHEM SOC LONDON, P327

[5] CLOURING MATTERS OF APHIDIDAE .30. COUPLING REACTIONS INVOLVING QUINONE A DERIVED BY REDUCTION OF PROTOAPHIN-FB [J].

BLACKBURN, GM ;

CAMERON, DW ;

CHAN, HWS .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1966, (20) :1836-+

[6] Synthesis of pyran and pyranone natural products [J].

Donner, CD ;

Gill, M ;

Tewierik, LM .

MOLECULES, 2004, 9 (06) :498-512

[7] 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

[8] STRUCTURE OF XYLINDEIN [J].

EDWARDS, RL ;

KALE, N .

TETRAHEDRON, 1965, 21 (08) :2095-&

[9] AN INVESTIGATION INTO THE FORMATION OF BENZO-PYRANS, AND NAPHTHO-PYRANS BY CYCLIZATION OF "ORTHO-ALKENYL(HYDROXYALKYL)BENZENES USING EITHER CERIUM(IV) AMMONIUM-NITRATE OR POTASSIUM TERT-BUTOXIDE IN DIMETHYLFORMAMIDE [J].

GILES, RGF ;

GREEN, IR ;

PESTANA, JAX .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (10) :2389-2395

[10]

GILES RGF, 1979, S AFR J CHEM, V32, P127

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