A short synthetic route to the tricyclic guanidinium core of the batzelladine alkaloids

被引：53

作者：

Black, GP

Murphy, PJ ^{[1
]}

Walshe, NDA

机构：

[1] Univ Wales, Dept Chem, Bangor LL57 2UW, Gwynedd, Wales

[2] Pfizer Ltd, Cent Res, Sandwich CT13 9NJ, Kent, England

来源：

TETRAHEDRON | 1998年 / 54卷 / 32期

关键词：

alkaloids; guanidines; Michael reactions;

D O I：

10.1016/S0040-4020(98)00576-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition of guanidine to a series of bis-alpha,beta-unsaturated ketones is reported leading to the formation of tricyclic guanidines, which are models of the naturally occurring batzelladine alkaloids. Nmr evidence is given in support of a new assignment for the relative stereochemistry of batzelladine F. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：9481 / 9488

页数：8

相关论文

共 25 条

[1] 2 NEW GUANIDINE ALKALOIDS FROM THE MEDITERRANEAN SPONGE CRAMBE-CRAMBE [J].

BERLINCK, RGS ;

BRAEKMAN, JC ;

DALOZE, D ;

HALLENGA, K ;

OTTINGER, R ;

BRUNO, I ;

RICCIO, R .

TETRAHEDRON LETTERS, 1990, 31 (45) :6531-6534

[2]

BLACK GP, 1996, TETRAHEDRON LETT, V37, P6493

[3] TRIPHENYLPHOSPHINE OXIDE AS A CRYSTALLIZATION AID [J].

ETTER, MC ;

BAURES, PW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (02) :639-640

[4] PREPARATION AND REACTIONS OF DIALKOXYTETRAHYDROFURANS [J].

FAKSTORP, J ;

RALEIGH, D ;

SCHNIEPP, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (02) :869-875

[5] SYNTHESIS OF A STRUCTURAL ANALOG OF PTILOMYCALIN-A [J].

GRILLOT, AL ;

HART, DJ .

TETRAHEDRON, 1995, 51 (42) :11377-11392

[6] CRAMBESCIDINS - NEW ANTIVIRAL AND CYTOTOXIC COMPOUNDS FROM THE SPONGE CRAMBE-CRAMBE [J].

JARESERIJMAN, EA ;

SAKAI, R ;

RINEHART, KL .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (19) :5712-5715

[7]

KASHMAN Y, 1989, J AM CHEM SOC, V111, P892

[8] Studies towards the synthesis of guanidine alkaloids; Synthesis of a tricyclic guanidine from succinimide [J].

Louwrier, S ;

Ostendorf, M ;

Tuynman, A ;

Hiemstra, H .

TETRAHEDRON LETTERS, 1996, 37 (06) :905-908

[9]

Murphy P.J., 1996, J CHEM SOC CHEM COMM, P445

[10] Biomimetic model studies towards ptilomycalin A [J].

Murphy, PJ ;

Williams, HL ;

Hibbs, DE ;

Hursthouse, MB ;

Malik, KMA .

TETRAHEDRON, 1996, 52 (24) :8315-8332