First stereoselective syntheses of (-)-siphonodiol and (-)-tetrahydrosiphonodiol, bioactive polyacetylenes from marine sponges

被引：45

作者：

López, S ^{[1
]}

Fernández-Trillo, F ^{[1
]}

Midón, P ^{[1
]}

Castedo, L ^{[1
]}

Saá, C ^{[1
]}

机构：

[1] Univ Santiago de Compostela, Fac Quim, Dept Quim Organ, Santiago De Compostela 15782, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 16期

关键词：

D O I：

10.1021/jo050807f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first stereoselective total syntheses of the bioactive marine polyacetylenes (-)-siphonodiol and (-)-tetrahydrosiphonodiol were achieved using highly convergent approaches based on optimized Cadiot-Chodkiewicz and sequential Sonogashira cross-coupling reactions.

引用

页码：6346 / 6352

页数：7

共 42 条

[1] A convenient route to unsymmetrical conjugated diynes [J].

Alami, M ;

Ferri, F .

TETRAHEDRON LETTERS, 1996, 37 (16) :2763-2766

[2] AN EFFICIENT PALLADIUM-CATALYZED REACTION OF VINYL AND ARYL HALIDES OR TRIFLATES WITH TERMINAL ALKYNES [J].

ALAMI, M ;

FERRI, F ;

LINSTRUMELLE, G .

TETRAHEDRON LETTERS, 1993, 34 (40) :6403-6406

[3] A one-pot synthesis of 1-arylalka-1,3-diynes by sequential acetylene zipper and Sonogashira reactions [J].

Balova, IA ;

Morozkina, SN ;

Knight, DW ;

Vasilevsky, SF .

TETRAHEDRON LETTERS, 2003, 44 (01) :107-109

[4] A convenient synthesis of functionalised 1-aryl-1,3-alkadiynes [J].

Balova, IA ;

Sorokoumov, VN ;

Morozkina, SN ;

Vinogradova, OV ;

Knight, DW ;

Vasilevsky, SF .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (05) :882-888

[5] Marine natural products [J].

Blunt, JW ;

Copp, BR ;

Munro, MHG ;

Northcote, PT ;

Prinsep, MR .

NATURAL PRODUCT REPORTS, 2005, 22 (01) :15-61

[6]

COREY EJ, 1972, TETRAHEDRON LETT, P3769

[7] Asymmetric synthesis of the chlorocyclopropane containing callipeltoside A side chain [J].

Evans, DA ;

Burch, JD .

ORGANIC LETTERS, 2001, 3 (04) :503-505

[8] A straightforward method for the synthesis of unsymmetrically substituted 1,3-diynes [J].

Fiandanese, V ;

Bottalico, D ;

Marchese, G ;

Punzi, A .

TETRAHEDRON LETTERS, 2003, 44 (51) :9087-9090

[9] BIOACTIVE MARINE METABOLITES .21. H,K-ATPASE INHIBITORS FROM THE MARINE SPONGE SIPHONOCHALINA-TRUNCATA - ABSOLUTE-CONFIGURATION OF SIPHONODIOL AND 2 RELATED METABOLITES [J].

FUSETANI, N ;

SUGANO, M ;

MATSUNAGA, S ;

HASHIMOTO, K .

TETRAHEDRON LETTERS, 1987, 28 (37) :4311-4312

[10] Biofouling and antifouling [J].

Fusetani, N .

NATURAL PRODUCT REPORTS, 2004, 21 (01) :94-104

← 1 2 3 4 5 →