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

Christopher D. Donner; Anthony N. Cuzzupe; Cheryl L. Falzon; Melvyn Gill

doi:10.1016/j.tet.2012.02.009

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

Christopher D. Donner, Anthony N. Cuzzupe, Cheryl L. Falzon, Melvyn Gill

Research output: Contribution to journal › Article › Research › peer-review

25 Citations (Scopus)

Abstract

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 Diels-Alder cycloaddition processes. Methods for self-coupling of dihydroxynaphthoquinones to give extended quinones are explored.

Original language	English
Pages (from-to)	2799-2805
Number of pages	7
Journal	Tetrahedron
Volume	68
Issue number	13
DOIs	https://doi.org/10.1016/j.tet.2012.02.009
Publication status	Published - 1 Apr 2012
Externally published	Yes

Keywords

Diels-Alder
Extended quinone
Fungal pigment
Xylindein

Access to Document

10.1016/j.tet.2012.02.009

Cite this

@article{bc18aa41b02048f79caec4c3f7403e5c,

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

abstract = "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 Diels-Alder cycloaddition processes. Methods for self-coupling of dihydroxynaphthoquinones to give extended quinones are explored.",

keywords = "Diels-Alder, Extended quinone, Fungal pigment, Xylindein",

author = "Donner, {Christopher D.} and Cuzzupe, {Anthony N.} and Falzon, {Cheryl L.} and Melvyn Gill",

year = "2012",

month = apr,

day = "1",

doi = "10.1016/j.tet.2012.02.009",

language = "English",

volume = "68",

pages = "2799--2805",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "13",

}

TY - JOUR

T1 - Investigations towards the synthesis of xylindein, a blue-green pigment from the fungus Chlorociboria aeruginosa

AU - Donner, Christopher D.

AU - Cuzzupe, Anthony N.

AU - Falzon, Cheryl L.

AU - Gill, Melvyn

PY - 2012/4/1

Y1 - 2012/4/1

N2 - 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 Diels-Alder cycloaddition processes. Methods for self-coupling of dihydroxynaphthoquinones to give extended quinones are explored.

AB - 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 Diels-Alder cycloaddition processes. Methods for self-coupling of dihydroxynaphthoquinones to give extended quinones are explored.

KW - Diels-Alder

KW - Extended quinone

KW - Fungal pigment

KW - Xylindein

UR - http://www.scopus.com/inward/record.url?scp=84857924659&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2012.02.009

DO - 10.1016/j.tet.2012.02.009

M3 - Article

AN - SCOPUS:84857924659

SN - 0040-4020

VL - 68

SP - 2799

EP - 2805

JO - Tetrahedron

JF - Tetrahedron

IS - 13

ER -

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

Abstract

Keywords

Access to Document

Other files and links

Cite this