Pigments of fungi. XLVII - Cardinalic acid, a new anthraquinone carboxylic acid from the New Zealand toadstool Dermocybe cardinalis and the synthesis and X-ray crystal structure of methyl 1,7,8-tri-O-methylcardinalate

被引：3

作者：

Gill, M ^{[1
]}

Morgan, PM ^{[1
]}

White, JM ^{[1
]}

Yu, J ^{[1
]}

机构：

[1] Univ Melbourne, Sch Chem, Parkville, Vic 3052, Australia

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1998年 / 51卷 / 03期

关键词：

D O I：

10.1071/C97154

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cardinalic acid (1,7,8-trihydroxy-6-methoxy-3-methyl-9, 10-dioxoanthracene-2-carboxylic acid) (4) and the known anthraquinone carboxylic acids endocrocin (1), dermolutein (2) and cinnalutein (3) have been isolated from the New Zealand toadstool Dermocybe cardinalis. Methyl 1,7,8-tri-O-methylcardinalate (5) has been prepared both by permethylation of the natural product (4) and from 2,6-dichloro-1,4-benzoquinone by two consecutive regioselective Diels-Alder cycloaddition reactions. A single-crystal X-ray structure analysis of the ester (5) corroborates the structure of the natural product (4) and confirms the outcome of both cycloaddition reactions.

引用

页码：213 / 218

页数：6

共 6 条

[1] Pigments of fungi.: LVII -: Structure and X-ray crystallographic analysis of dermocanarin 10, a new naphthalene-dihydroanthracenone dimer from an Australian Dermocybe toadstool
Gill, M
Millar, PM
Phonh-Axa, S
Raudies, E
White, JM
Yu, J
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1999, 52 (09) : 881 - 884
[2] Crystal structure from laboratory X-ray powder diffraction data, DFT-D calculations, Hirshfeld surface analysis, and energy frameworks of a new polymorph of 1-benzothiophene-2-carboxylic acid
Dugarte-Dugarte, Analio J.
van de Streek, Jacco
Diaz de Delgado, Graciela
Rafalska-Lasocha, Alicja
Miguel Delgado, Jose
[J]. POWDER DIFFRACTION, 2021, 36 (01) : 2 - 13
[3] Pigments of fungi.: Part 70.: Total synthesis of (R)-semixanthomegnin and the X-ray crystal structure of (±)-7-chloro-10-methoxy-3-methyl-3, 4-dihydro-1H-naphtho[2,3-c]pyran-1,6,9-trione
Cotterill, AS
Donner, CD
Gill, M
White, JM
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 2003, 56 (01) : 49 - 57
[4] Synthesis of a new chiral source, (1R,2S)-1-phenylphospholane-2-carboxylic acid, via a key intermediate α-phenylphospholanyllithium borane complex:: Configurational stability and X-ray crystal structure of an α-monophosphinoalkyllithium borane complex
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[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (01) : 361 - 368
[5] Pigments of fungi.: Part 70.: Total synthesis of (R)-semixanthomegnin and the X-ray crystal structure of (±)-7-chloro-10-methoxy-3-methyl-3,4-dihydro-1H- naphtho[2,3-c]pyran-1,6,9-trione (vol 56, pg 49, 2003)
Cotterill, AS
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[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 2003, 56 (06) : CP4 - CP4
[6] Crystal structure from laboratory X-ray powder diffraction data, DFT-D calculations, Hirshfeld surface analysis, and energy frameworks of a new polymorph of 1-benzothiophene-2-carboxylic acid (vol 36, pg 2, 2020)
Dugarte-Dugarte, Analio J.
van de Streek, Jacco
Diaz de Delgado, Graciela
Rafalska-Lasocha, Alicja
Delgado, Jose Miguel
[J]. POWDER DIFFRACTION, 2021, 36 (03) : 219 - 219

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