Synthesis of the potent antitumoral marine alkaloid variolin B

被引：33

作者：

Molina, P ^{[1
]}

Fresneda, PM ^{[1
]}

Delgado, S ^{[1
]}

Bleda, JA ^{[1
]}

机构：

[1] Univ Murcia, Fac Quim, Dept Quim Organ, E-30100 Murcia, Spain

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 06期

关键词：

phosphine imines; natural products; sponges; decarboxylation; pyrimidines;

D O I：

10.1016/S0040-4039(01)02321-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of the marine alkaloid variolin B has been completed in seven steps, starting from the iminophosphorane derived from ethyl alpha-azido-beta-(4-methoxy-7-azaindol-3-yl) acrylate, available by condensation of 2-formyl-4-methoxy-7-aza-indole with ethyl azidoacetate. Formation of the annulated 2-aminopyrimidine ring is achieved by tandem aza-Wittig/carbodiimide-mediated cyclization whereas the 2-aminopyrimidine substituent at C-5 is formed using an acetyl group as C, moiety of the pyrimidine ring. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：1005 / 1007

页数：3

相关论文

共 15 条

[1]

ALBIZATI KF, 1992, SYNTHESIS MARINE NAT, V6, P158

[2] Synthesis of deoxyvariolin B [J].

Alvarez, M ;

Fernández, D ;

Joule, JA .

TETRAHEDRON LETTERS, 2001, 42 (02) :315-317

[3] Total synthesis of variolin B [J].

Anderson, RJ ;

Morris, JC .

TETRAHEDRON LETTERS, 2001, 42 (49) :8697-8699

[4] Studies toward the total synthesis of the variolins: rapid entry to the core structure [J].

Anderson, RJ ;

Morris, JC .

TETRAHEDRON LETTERS, 2001, 42 (02) :311-313

[5] UMSETZUNGEN VON VINYLOGEN CARBONSAUREAMIDEN ZU HETEROCYCLEN [J].

BREDERECK, H ;

EFFENBERGER, F ;

BOTSCH, H ;

REHN, H .

CHEMISCHE BERICHTE-RECUEIL, 1965, 98 (04) :1081-+

[6] Marine natural products [J].

Faulkner, DJ .

NATURAL PRODUCT REPORTS, 2001, 18 (01) :1-49

[7] Indole alkaloids from the tunicate Aplidium meridianum [J].

Franco, LH ;

Joffé, EBD ;

Puricelli, L ;

Tatian, M ;

Seldes, AM ;

Palermo, JA .

JOURNAL OF NATURAL PRODUCTS, 1998, 61 (09) :1130-1132

[8] Synthesis of the indole alkaloids meridianins from the tunicate Aplidium meridianum [J].

Fresneda, PM ;

Molina, P ;

Bleda, JA .

TETRAHEDRON, 2001, 57 (12) :2355-2363

[9] Synthetic studies towards the 2-aminopyrimidine alkaloids variolins and meridianins from marine origin [J].

Fresneda, PM ;

Molina, P ;

Delgado, S ;

Bleda, JA .

TETRAHEDRON LETTERS, 2000, 41 (24) :4777-4780

[10] Reaction of 2-bromomethylazoles and TosMIC: A domino process to azolopyrimidines. Synthesis of core tricycle of the variolins alkaloids [J].

Mendiola, J ;

Minguez, JM ;

Alvarez-Builla, J ;

Vaquero, JJ .

ORGANIC LETTERS, 2000, 2 (21) :3253-3256