Synthesis of pyran and pyranone natural products

被引：41

作者：

Donner, CD ^{[1
]}

Gill, M ^{[1
]}

Tewierik, LM ^{[1
]}

机构：

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

来源：

MOLECULES | 2004年 / 9卷 / 06期

关键词：

stereospecific synthesis; fungal metabolites; quinones; isochromanones;

D O I：

10.3390/90600498

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

An overview of the synthesis of the fungal metabolites (+)-dermolactone, (-)-semixanthomegnin, (+)- and (-)-mellein, (-)-ochratoxin alpha, (-)-(1R,3S)-thysanone, the enantiopure ventiloquinones L, E and G, and 8-desmethyleleutherin from a common chiral intermediate, is presented. Further methodology leading potentially toward extended quinones such as (3S,3'S)-xylindein is also outlined.

引用

页码：498 / 512

页数：15

共 35 条

[1]

BENFORD D, 2001, FAO FOOD NUTR PAP, V74, P281

[2]

BLACKBUR.GM, 1965, CHIMIA, V19, P208

[3]

BLACKBURN GM, 1962, P CHEM SOC LONDON, P327

[4] Synthetic strategies towards pyranonaphthoquinone antibiotics [J].

Brimble, MA ;

Nairn, MR ;

Prabaharan, H .

TETRAHEDRON, 2000, 56 (14) :1937-1992

[5] Pigments of fungi. XLV - The cardinalins 8-12, unique pre-naphthoquinone dehydro dimers from the New Zealand toadstool Dermocybe cardinalis [J].

Buchanan, MS ;

Gill, M ;

Yu, J .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1997, 50 (11) :1081-1089

[6] Pigments of fungi .43. Cardinalins-1-6, novel pyranonaphthoquinones from the fungus Dermocybe cardinalis Horak [J].

Buchanan, MS ;

Gill, M ;

Yu, J .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (06) :919-925

[7]

CARLSON RM, 1974, TETRAHEDRON LETT, V15, P2615

[8] REACTIONS OF THE CARBANION FROM AN ORSELLINATE DERIVATIVE WITH ELECTROPHILES [J].

CARPENTER, TA ;

EVANS, GE ;

LEEPER, FJ ;

STAUNTON, J ;

WILKINSON, MR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (05) :1043-1051

[9] 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 [J].

Cotterill, AS ;

Donner, CD ;

Gill, M ;

White, JM .

AUSTRALIAN JOURNAL OF CHEMISTRY, 2003, 56 (01) :49-57

[10] PIGMENTS OF FUNGI .41. SYNTHESIS OF (S)-(+)-DERMOLACTONE AND (+/-)-DERMOLACTONE - STEREOCHEMISTRY OF DERMOLACTONE FROM THE AUSTRALIAN FUNGUS DERMOCYBE-SANGUINEA (WULF EX FR) WUNSCHE SENSU CLELAND [J].

COTTERILL, AS ;

GILL, M ;

MILANOVIC, NM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (10) :1215-1223

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