BIOMIMETIC SYNTHESIS OF THEONELLIN ISOCYANIDE

被引：28

作者：

ICHIKAWA, Y ^{[1
]}

机构：

[1] MIE UNIV, FAC EDUC, TSU, MIE 514, JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 16期

关键词：

D O I：

10.1039/p19920002135

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A marine sesquiterpene of the theonellin class has been synthesized for the first time. Direct amination of the theonelline carbon framework 2 in a biomimetic fashion, a crucial step, was achieved by employing a triflic acid-promoted Ritter-type reaction at low temperature (-78-degrees-C).

引用

页码：2135 / 2139

页数：5

共 12 条

[1] NEW PREPARATION OF ISOCYANIDES [J].

APPEL, R ;

KLEINSTUCK, R ;

ZIEHN, KD .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1971, 10 (02) :132-+

[2]

BALDWIN JE, 1990, SYNLETT, P603

[3]

BURRESON BJ, 1975, TETRAHEDRON, V31, P2018

[4]

DELAY F, 1979, HELV CHIM ACTA, V38, P369

[5] BIOSYNTHESIS OF DIISOCYANOADOCIANE, A NOVEL DITERPENE FROM THE MARINE SPONGE AMPHIMEDON SP CRYSTAL-STRUCTURE OF A MONOAMIDE DERIVATIVE [J].

FOOKES, CJR ;

GARSON, MJ ;

MACLEOD, JK ;

SKELTON, BW ;

WHITE, AH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (05) :1003-1011

[6]

GASON MJ, 1989, NAT PROD REP, V6, P143

[7] NITROGENOUS BISABOLENE SESQUITERPENES FROM MARINE-INVERTEBRATES [J].

GULAVITA, NK ;

DESILVA, ED ;

HAGADONE, MR ;

KARUSO, P ;

SCHEUER, PJ ;

VANDUYNE, GD ;

CLARDY, J .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (26) :5136-5139

[8] FORMYLATION OF AMINES [J].

HUFFMAN, CW .

JOURNAL OF ORGANIC CHEMISTRY, 1958, 23 (05) :727-729

[9] THE INFLUENCE OF CHAIN-BRANCHING ON THE STERIC OUTCOME OF SOME OLEFIN-FORMING REACTIONS [J].

KOCIENSKI, PJ ;

LYTHGOE, B ;

WATERHOUSE, I .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (04) :1045-1050

[10]

Krimen L. I., 1969, ORG REACTIONS, V17, P213, DOI DOI 10.1002/0471264180.0R017.03

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