CHEMISTRY OF TRICARBONYL HEMIKETALS AND APPLICATION OF EVANS TECHNOLOGY TO THE TOTAL SYNTHESIS OF THE IMMUNOSUPPRESSANT (-)-FK-506

被引:179
作者
JONES, TK
REAMER, RA
DESMOND, R
MILLS, SG
机构
[1] Merck Sharp & Dohme Research Laboratories, Rahway New Jersey
关键词
D O I
10.1021/ja00164a023
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Details of model studies probing the chemistry of the tricarbonyl region of FK-506 are presented, and their use in designing a successful route to this immunosuppressant is outlined. Applications of asymmetric oxazolidinone alkylation/aldol methodology to a convergent, highly flexible synthesis of the C10-C18 fragment and to improvements in the preparation of the C20-C34 segment are also discussed. © 1990, American Chemical Society. All rights reserved.
引用
收藏
页码:2998 / 3017
页数:20
相关论文
共 62 条
[1]   OXIDATION OF VICINAL DIOLS TO ALPHA-DICARBONYL COMPOUNDS BY TRIFLUOROACETIC-ANHYDRIDE ACTIVATED DIMETHYLSULFOXIDE [J].
AMON, CM ;
BANWELL, MG ;
GRAVATT, GL .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (22) :4851-4855
[2]   A DIASTEREOSPECIFIC, NON-RACEMIC SYNTHESIS OF THE C.10-C.18 SEGMENT OF FK-506 [J].
ASKIN, D ;
VOLANTE, RP ;
REAMER, RA ;
RYAN, KM ;
SHINKAI, I .
TETRAHEDRON LETTERS, 1988, 29 (03) :277-280
[3]   CHEMISTRY OF FK-506 - BENZILIC ACID REARRANGEMENT OF THE TRICARBONYL SYSTEM [J].
ASKIN, D ;
REAMER, RA ;
JONES, TK ;
VOLANTE, RP ;
SHINKAI, I .
TETRAHEDRON LETTERS, 1989, 30 (06) :671-674
[4]   ALKYLATION OF CHIRAL PROLINOL PROPIONAMIDE ENOLATES WITH EPOXIDES - COMPLETE REVERSAL OF PREDICTED FACIAL SELECTIVITY [J].
ASKIN, D ;
VOLANTE, RP ;
RYAN, KM ;
REAMER, RA ;
SHINKAI, I .
TETRAHEDRON LETTERS, 1988, 29 (34) :4245-4248
[5]   FACILE SYNTHESIS OF CARBOXAMIDES BY USING 1-METHYL-2-HALOPYRIDINIUM IODIDES AS COUPLING REAGENTS [J].
BALD, E ;
SAIGO, K ;
MUKAIYAMA, T .
CHEMISTRY LETTERS, 1975, (11) :1163-1166
[6]  
BASHA A, 1977, TETRAHEDRON LETT, P4171
[7]   CHIRAL ECONOMIC SYNTHESIS OF (R)-MUSCONE AND (S)-MUSCONE USING CYCLOFRAGMENTATION OF EPOXYSULFONES [J].
BRANCA, Q ;
FISCHLI, A .
HELVETICA CHIMICA ACTA, 1977, 60 (03) :925-944
[8]  
BUSS AD, 1981, J CHEM SOC CHEM COMM, P100
[9]   CIS-OLEFINS FROM THE HORNER-WITTIG REACTION - ORIGIN AND OPTIMIZATION OF STEREOCHEMISTRY [J].
BUSS, AD ;
WARREN, S .
TETRAHEDRON LETTERS, 1983, 24 (36) :3931-3934
[10]  
COLEMAN RS, 1989, HETEROCYCLES, V28, P157