Synthesis of model ring systems related to C10-C18 analogues of the mycalamides/theopederins

被引：16

作者：

Gardiner, JM ^{[1
]}

Mills, R ^{[1
]}

Fessard, T ^{[1
]}

机构：

[1] UMIST, Dept Chem, Manchester M60 1QD, Lancs, England

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 06期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/j.tetlet.2003.11.141

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conjugate addition to D-galactose-derived pyranones 8 and 10, with in situ enolate alkylation, or protonation, provides pyranones 11-13 or 16-19. These are related to the C10-C18 fragment of the mycalamides and provide a short entry to C10, C11, C14 and C15 stereocentres. This approach is relevant to introduction of the side-chain and analogues thereof, and allows for variable C14 functionality. Two side-chain analogues, both C14 monomethylated diastereomers, the C14 unsubstituted system and the natural product-related C14 dimethyl functionality are prepared, and C13 epimeric functionality introduced. (C) 2003 Elsevier Ltd. All rights reserved.

引用

收藏

页码：1215 / 1217

页数：3

相关论文

共 28 条

[1] Chemistry of the mycalamides: Antiviral and antitumour compounds from a New Zealand marine sponge .6. The synthesis and testing of analogues of the C(7)-C(10) fragment [J].

Abell, AD ;

Blunt, JW ;

Foulds, GJ ;

Munro, MHG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (11) :1647-1654

[2] NEW SYNTHETIC APPLICATIONS OF ORGANOTIN COMPOUNDS - SYNTHESIS OF STEREODEFINED 2-IODO-2-ALKENONES, 2-SUBSTITUTED (E)-2-ALKENONES AND 2-METHYL-2-CYCLOALKENONES [J].

BELLINA, F ;

CARPITA, A ;

CIUCCI, D ;

DESANTIS, M ;

ROSSI, R .

TETRAHEDRON, 1993, 49 (21) :4677-4698

[3]

Breitfelder S, 1998, SYNTHESIS-STUTTGART, P468

[4]

BURRES NS, 1989, CANCER RES, V49, P2935

[5]

Cardani C., 1965, TETRAHEDRON LETT, V6, P2537

[6] AN IMPROVED SYNTHESIS AND NMR-SPECTRA OF BENZYLATED GLYCALS [J].

CHMIELEWSKI, M ;

FOKT, I ;

GRODNER, J ;

GRYNKIEWICZ, G ;

SZEJA, W .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1989, 8 (05) :735-741

[7] LARGE RATE ACCELERATIONS IN THE STILLE REACTION WITH TRI-2-FURYLPHOSPHINE AND TRIPHENYLARSINE AS PALLADIUM LIGANDS - MECHANISTIC AND SYNTHETIC IMPLICATIONS [J].

FARINA, V ;

KRISHNAN, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (25) :9585-9595

[8] Synthesis and biological activity of artificial analogs of mycalamide A [J].

Fukui, H ;

Tsuchiya, Y ;

Fujita, K ;

Nakagawa, T ;

Koshino, H ;

Nakata, T .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (16) :2081-2086

[9] BIOACTIVE MARINE METABOLITES SERIES .41. THEOPEDERINS-A-E, POTENT ANTITUMOR METABOLITES FROM A MARINE SPONGE, THEONELLA SP [J].

FUSETANI, N ;

SUGAWARA, T ;

MATSUNAGA, S .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14) :3828-3832

[10] EFFECTS OF CYCLOSPORINE-A, FK-506, AND MYCALAMIDE-A ON THE ACTIVATION OF MURINE-CD4+ T-CELLS BY THE MURINE B7-ANTIGEN [J].

GALVIN, F ;

FREEMAN, GJ ;

RAZIWOLF, Z ;

BENACERRAF, B ;

NADLER, L ;

REISER, H .

EUROPEAN JOURNAL OF IMMUNOLOGY, 1993, 23 (01) :283-286