STEREOSELECTIVE SYNTHESIS OF LYCORANES (2,3,3A,4,5,7-TETRAHYDRO-1H-PYR-ROLO[3,2,1-DE]PHENANTHRIDINES) DERIVED FROM ALKALOIDS LYCORINE AND CARANINE

被引：15

作者：

TANAKA, H ^{[1
]}

NAGAI, Y ^{[1
]}

IRIE, H ^{[1
]}

UYEO, S ^{[1
]}

KUNO, A ^{[1
]}

机构：

[1] KYOTO UNIV,FAC PHARMACEUT SCI,KYOTO 606,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1979年 / 04期

关键词：

D O I：

10.1039/p19790000874

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Three stereoisomeric lycoranes (2,3,3a,4,5,7-tetrahydro-1H-pyrrolo[3,2,1- de]phenanthridines), α-, β-, and δ-lycorane, derived from the Amaryllidaceae alkaloids lycorine and caranine were stereoselectively synthesised from two stereoisomeric 3-(3,4-methylenedioxyphenyl)-1,2,3,6- tetrahydrophthalic anhydrides obtained by Diels-Alder reaction of 1-(3,4-methylenedioxyphenyl)but-3-en-1-ol and fumaric acid.

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页码：874 / 878

页数：5

相关论文

共 20 条

[1] LYCORINE - STUDIES IN SYNTHESIS [J].

DYKE, SF ;

SAINSBURY, M ;

EVANS, JR .

TETRAHEDRON, 1973, 29 (01) :213-220

[2]

GANEM B, 1971, TETRAHEDRON LETT, P4105

[3] The constituents of natural phenolic resins Part XVIII 1 2 3 4-tetrahydronaphthalene-2 3-dicarboxylic acid and the 1-phenyl derivative [J].

Haworth, RD ;

Slinger, FH .

JOURNAL OF THE CHEMICAL SOCIETY, 1940, :1321-1327

[4] AMARYLLIDACEOUS ALKALOIDS - TOTAL SYNTHESIS OF DIHYDROXYCRINENE [J].

HENDRICK.JB ;

FOOTE, C ;

YOSHIMUR.N .

CHEMICAL COMMUNICATIONS, 1965, (09) :165-&

[5] SOME APPROACHES TO TOTAL SYNTHESIS OF LYCORINE [J].

HENDRICKSON, JB ;

ALDER, RW ;

DALTON, DR ;

HEY, DG .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2667-+

[6] STEREOSPECIFIC SYNTHESIS OF HAEMANTHIDINE AND TAZETTINE [J].

HENDRICKSON, JB ;

BOGARD, TL ;

FISCH, ME .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (18) :5538-+

[7] STEREOSELECTIVE SYNTHESES OF D,L-ALPHA- AND BETA-LYCORANES [J].

HILL, RK ;

JOULE, JA ;

LOEFFLER, LJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (24) :4951-&

[8] PHOTOCYCLIZATION OF ENAMIDO-KETONES - NOVEL SYNTHESIS OF LYCORINE-TYPE ALKALOIDS [J].

IIDA, H ;

AOYAGI, S ;

KIBAYASHI, C .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1974, (13) :499-499

[9] SYNTHESIS OF DELTA-LYCORANE DERIVED FROM ALKALOID CARANINE [J].

IRIE, H ;

SUGITA, M ;

TAMOTO, K ;

UYEO, S ;

NISHITANI, Y .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1972, (04) :588-+

[10] TOTAL SYNTHESIS OF ALKALOIDS CLIVONINE AND CLIVIDINE [J].

IRIE, H ;

NAGAI, Y ;

TAMOTO, K ;

TANAKA, H .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (09) :302-303