Studies toward the total synthesis of the variolins: rapid entry to the core structure

被引：24

作者：

Anderson, RJ ^{[1
]}

Morris, JC ^{[1
]}

机构：

[1] Univ Canterbury, Dept Chem, Christchurch 1, New Zealand

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 02期

关键词：

alkaloids; pyridines; pyrimidines; deoxygenation; cyclization;

D O I：

10.1016/S0040-4039(00)01772-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine core structure of the variolins has been synthesized in three steps from commercially available materials. The key reaction involves the deoxygenation and concomitant cyclization of a triarylmethanol using the combination of triethylsilane and trifluoroacetic acid. Introduction of amine functionality as required for the natural products has been achieved in two steps. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：311 / 313

页数：3

共 9 条

[1] Synthesis of deoxyvariolin B [J].

Alvarez, M ;

Fernández, D ;

Joule, JA .

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

[2]

Alvarez M, 1999, SYNTHESIS-STUTTGART, P615

[3] Synthesis of 1,2-dihydropyrrolo[1,2-c]pyrimidin-1-ones [J].

Alvarez, M ;

Fernández, D ;

Joule, JA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (03) :249-255

[4] 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

[5]

KURSANOV DN, 1974, SYNTHESIS-STUTTGART, P633

[6] STANNYLATION REACTIONS AND CROSS-COUPLINGS IN PYRIMIDINES [J].

MAJEED, AJ ;

ANTONSEN, O ;

BENNECHE, T ;

UNDHEIM, K .

TETRAHEDRON, 1989, 45 (04) :993-1006

[7] ALKALOIDS FROM THE ANTARCTIC SPONGE KIRKPATRICKIA-VARIALOSA .1. VARIOLIN-B, A NEW ANTITUMOR AND ANTIVIRAL COMPOUND [J].

PERRY, NB ;

ETTOUATI, L ;

LITAUDON, M ;

BLUNT, JW ;

MUNRO, MHG ;

PARKIN, S ;

HOPE, H .

TETRAHEDRON, 1994, 50 (13) :3987-3992

[8]

PRITCHARD D, 1999, J CHEM SOC P1, P855

[9] ALKALOIDS FROM THE ANTARCTIC SPONGE KIRKPATRICKIA-VARIALOSA .2. VARIOLIN-A AND N(3')-METHYL TETRAHYDROVARIOLIN-B [J].

TRIMURTULU, G ;

FAULKNER, DJ ;

PERRY, NB ;

ETTOUATI, L ;

LITAUDON, M ;

BLUNT, JW ;

MUNRO, MHG ;

JAMESON, GB .

TETRAHEDRON, 1994, 50 (13) :3993-4000

← 1 →