SYNTHESIS OF MINOR XANTHONES FROM GARCINIA-MANGOSTANA

被引：26

作者：

BENNETT, GJ ^{[1
]}

LEE, HH ^{[1
]}

LEE, LP ^{[1
]}

机构：

[1] NATL UNIV SINGAPORE,DEPT CHEM,SINGAPORE 0511,SINGAPORE

来源：

JOURNAL OF NATURAL PRODUCTS | 1990年 / 53卷 / 06期

关键词：

D O I：

10.1021/np50072a010

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

Reaction of 2,3,6-trimethoxybenzoic acid and phloroglucinol in the presence of P2O5 and MeSO3H afforded 1,3-dihydroxy-5,8-dimethoxyxanthone [8] which, on 3-methylbut-2-enylation followed by methylation, gave a mixture of the mono- and di-(3-methylbut-2-enyl)xanthones 2, 5, 6, and 12. Whereas demethylation of xanthone 2 with hot aqueous morpholine yielded gartanin [1] and its 5-0-methylether 3, similar reaction of xanthone 5 gave, in addition to the expected products 14 and 15, two 1,3,7,8-tetraoxygenated xanthones 16 and 17. Selective methylation of 14 gave the natural xanthone 4.

引用

页码：1463 / 1470

页数：8

共 30 条

[1] SYNTHESIS OF 8-DEOXYGARTANIN - TRAPEZIFOLIXANTHONE AND RELATED XANTHONES [J].

ANAND, SM ;

JAIN, AC .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1974, 27 (07) :1515-1520

[2]

ANAND SM, 1973, INDIAN J CHEM, V11, P1233

[3] APPLICATIONS OF PROTON MAGNETIC RESONANCE SPECTROSCOPY IN STRUCTURAL INVESTIGATION OF XANTHONES [J].

BARRACLOUGH, D ;

LOCKSLEY, HD ;

SCHEINMANN, F ;

MAGALHAES, MT ;

GOTTLIEB, OR .

JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1970, (04) :603-+

[4] REARRANGEMENT OF 1,3,5,8-TETRAOXYGENATED XANTHONES IN HOT AQUEOUS MORPHOLINE [J].

BENNETT, GJ ;

LEE, HH .

TETRAHEDRON LETTERS, 1989, 30 (51) :7265-7268

[5] XANTHONES FROM GUTTIFERAE [J].

BENNETT, GJ ;

LEE, HH .

PHYTOCHEMISTRY, 1989, 28 (04) :967-998

[6]

BENNETT GJ, 1990, THESIS NATIONAL U SI, P153

[7] STUDIES IN XANTHONE SERIES .6. CLAISEN REARRANGEMENTS SELECTIVE DEMETHYLATIONS AND SYNTHESIS OF DIHYDROISOJACAREUBIN AND ALVAXANTHONE TRIMETHYL ETHER [J].

BURLING, ED ;

JEFFERSON, A ;

SCHEINMANN, F .

TETRAHEDRON, 1965, 21 (09) :2653-+

[8] SELECTIVE DEMETHYLATION OF POLYMETHOXYXANTHONES WITH AQUEOUS PIPERIDINE [J].

CHAUDHURI, RK ;

ZYMALKOWSKI, F ;

GHOSAL, S .

JOURNAL OF PHARMACEUTICAL SCIENCES, 1978, 67 (09) :1321-1322

[9] STUDIES ON CHEMICAL CONSTITUENTS OF CENTIANACEAE .1. XANTHONES OF CANSCORA-DECUSSATA SCHULT [J].

CHAUDHURI, RK .

PHYTOCHEMISTRY, 1971, 10 (10) :2425-+

[10]

DALAL SR, 1957, CHEM IND-LONDON, P140

← 1 2 3 →