SYNTHESIS OF DERIVATIVES OF FK-506 AND FR-900520 - MODIFICATIONS AT THE BINDING DOMAIN

被引：18

作者：

EMMER, G

WEBERROTH, S

机构：

[1] Sandoz Forschungsinstitut, A-1230 Wien

来源：

TETRAHEDRON | 1992年 / 48卷 / 28期

关键词：

FK-506; FR-900520; 9-DEOXO-FK-506; 9-DEOXO-FR-900520; RADICAL DEOXYGENATION;

D O I：

10.1016/S0040-4020(01)90178-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of 9-deoxo-FK 506 (13a), 9-deoxo-FR 900520 (13b), 9-deoxo-10(R)-deoxy-FR 900520 (14) and its 10(S) isomer 15 is described. Radical deoxygenation/elemination of the 9-di-hydro-9,10-thiocarbonates 5a,5b,6a and 6b gave the 9,10 unsaturated compounds 7a (7b) or 8a (8b) which were further transferred by hydration or hydrogenation. Different E/Z ratios of 7a (7b) were obtainted when nBu3SnH or [(CH3)3Si]3SiH in combination with AIBN or Et3B were used, allowing the selective preparation of both isomers. Two possible reaction mechanisms are discussed.

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页码：5861 / 5874

页数：14

相关论文

共 31 条

[11] CONFORMATION OF GLYCOSYL RADICALS - RADICAL STABILIZATION BY BETA-CO BONDS [J].

DUPUIS, J ;

GIESE, B ;

RUEGGE, D ;

FISCHER, H ;

KORTH, HG ;

SUSTMANN, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (11) :896-898

[12]

Dupuis J, 1984, ANGEW CHEM, V96, P887

[13] POLAR PARAMETERS FOR RADICAL SUBSTITUENTS [J].

GIESE, B ;

MEHL, W .

TETRAHEDRON LETTERS, 1991, 32 (34) :4275-4278

[14]

Kuivila H. G., 1970, SYNTHESIS-STUTTGART, P499

[15] CALCINEURIN IS A COMMON TARGET OF CYCLOPHILIN-CYCLOSPORINE-A AND FKBP-FK506 COMPLEXES [J].

LIU, J ;

FARMER, JD ;

LANE, WS ;

FRIEDMAN, J ;

WEISSMAN, I ;

SCHREIBER, SL .

CELL, 1991, 66 (04) :807-815

[16] SOLUTION STRUCTURE OF FKBP, A ROTAMASE ENZYME AND RECEPTOR FOR FK506 AND RAPAMYCIN [J].

MICHNICK, SW ;

ROSEN, MK ;

WANDLESS, TJ ;

KARPLUS, M ;

SCHREIBER, SL .

SCIENCE, 1991, 252 (5007) :836-839

[17] TRIALKYLBORANE AS AN INITIATOR AND TERMINATOR OF FREE-RADICAL REACTIONS - FACILE ROUTES TO BORON ENOLATES VIA ALPHA-CARBONYL RADICALS AND ALDOL REACTION OF BORON ENOLATES [J].

NOZAKI, K ;

OSHIMA, K ;

UTIMOTO, K .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1991, 64 (02) :403-409

[18] FACILE REDUCTION OF DITHIOCARBONATES DERIVED FROM SECONDARY ALCOHOLS WITH NORMAL-BU3SNH-ET3B AND SYNTHESIS OF 2-FURANTHIONES AND 2-FURANONES BY INTRAMOLECULAR ADDITION OF ALKOXYTHIOCARBONYL FREE-RADICALS TO ACETYLENIC LINKAGES [J].

NOZAKI, K ;

OSHIMA, K ;

UTIMOTO, K .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (09) :2578-2583

[19] FACILE REDUCTION OF DITHIOCARBONATES WITH NORMAL-BU3SNH-ET3B - EASY ACCESS TO HYDROCARBONS FROM SECONDARY ALCOHOLS [J].

NOZAKI, K ;

OSHIMA, K ;

UTIMOTO, K .

TETRAHEDRON LETTERS, 1988, 29 (47) :6125-6126

[20] REDUCTION OF CARBONYL-COMPOUNDS VIA HYDROSILYLATION .4. HIGHLY REGIOSELECTIVE REDUCTIONS OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS [J].

OJIMA, I ;

KOGURE, T .

ORGANOMETALLICS, 1982, 1 (10) :1390-1399

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