Pigments of fungi.: LII -: Anisochiral flavomannin 6,6′,8-tri-O-methyl ether from an Australian Dermocybe toadstool

被引:8
作者
Buchanan, MS [1 ]
Gill, M [1 ]
Gimenez, A [1 ]
Palfreyman, AR [1 ]
Phonh-Axa, S [1 ]
Raudies, E [1 ]
Yu, J [1 ]
机构
[1] Univ Melbourne, Sch Chem, Parkville, Vic 3052, Australia
关键词
D O I
10.1071/CH98172
中图分类号
O6 [化学];
学科分类号
0703 [化学];
摘要
Flavomannin 6,6',8-tri-O-methyl ether occurs in the fruiting bodies of the Australian toadstool Dermocybe sp. WAT 24274 as an anisochiral mixture of the (3S,3'S,P)- and (3R,3'R,M)-enantiomers (5) and (7), respectively, in which the former predominates to the extent of 50% e.e. The structure of the natural product is determined by spectroscopic methods and the absolute configuration and enantiomeric purity are deduced from the c.d. spectrum and by chemical degradation of the natural product to a mixture of stereoisomeric dihydroanthracenones that has been analysed by chiral h.p.l.c.
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收藏
页码:749 / 753
页数:5
相关论文
共 14 条
[1]
Pigments of fungi.: Part 51.: Structure and stereochemistry of coupled pre-anthraquinones of the pseudophlegmacin type from Australian toadstools belonging to the genus Dermocybe [J].
Buchanan, MS ;
Gill, M ;
Millar, PA ;
Phonh-Axa, S ;
Raudies, E ;
Yu, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (07) :795-801
[2]
Pigments of fungi.: Part 50.: Structure, biosynthesis and stereochemistry of new dimeric dihydroanthracenones of the phlegmacin type from Cortinarius sinapicolor Cleland [J].
Elsworth, C ;
Gill, M ;
Giménez, A ;
Milanovic, NM ;
Raudies, E .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (02) :119-125
[3]
INVITED REVIEW - PIGMENTS OF AUSTRALASIAN DERMOCYBE TOADSTOOLS [J].
GILL, M .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1995, 48 (01) :1-26
[4]
PIGMENTS OF FUNGI .19. A DEGRADATIVE METHOD FOR THE DETERMINATION OF CENTRAL CHIRALITY IN NATURALLY-OCCURRING 3-HYDROXY-3-METHYL-3,4-DIHYDROANTHRACEN-1(2H)-ONES - APPLICATION TO PIGMENTS OF THE FLAVOMANNIN TYPE [J].
GILL, M ;
GIMENEZ, A ;
JHINGRAN, AG ;
PALFREYMAN, AR .
TETRAHEDRON-ASYMMETRY, 1990, 1 (09) :621-634
[5]
GILL M, 1989, PHYTOCHEMISTRY, V28, P2847
[6]
GILL M, 1987, FORTSCHR CHEM ORG NA, V51, P125
[7]
HARADA N, 1993, CIRCULARLY DICHROIC
[8]
Helmchen G., 1982, ANGEW CHEM, V94, P614
[9]
JAGERS E, 1980, THESIS U BONN
[10]
OPTICAL-ACTIVITY IN BIARYL SERIES [J].
MASON, SF ;
SEAL, RH ;
ROBERTS, DR .
TETRAHEDRON, 1974, 30 (12) :1671-1682