AN APPROACH TO THE CYCLOHEXYL MOIETY OF THE IMMUNOSUPPRESSIVE AGENT FK-506

被引:13
作者
PEARSON, AJ
RODEN, BA
机构
[1] Department of Chemistry, Case Western Reserve University, Cleveland
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 03期
关键词
D O I
10.1039/p19900000723
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Tricarbonyl(3-methoxycyclohexadienyl)iron hexafluorophosphate, which is readily prepared from 1, 3-dimethoxybenzene, was treated with the enolate of methyl phenylsulphonylacetate to give an adduct which was decarboxylated and decomplexed to give 5-phenylsulphonylmethylcyclohexenone. This compound was converted by a four-step, highly stereoselective, sequence to the trisubstituted cyclohexane (2), which represents a cyclohexyl moiety building block for FK-506.
引用
收藏
页码:723 / 725
页数:3
相关论文
共 26 条
[1]   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
[2]   SYNTHETIC ROUTE TO THE TRICARBONYL REGION OF FK-506 [J].
EGBERTSON, M ;
DANISHEFSKY, SJ .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (01) :11-12
[3]  
Evans D. A., 1982, ALDRICHIM ACTA, V15, P23
[4]   ALDOL ADDITION-REACTIONS OF CHIRAL CROTONATE IMIDES [J].
EVANS, DA ;
SJOGREN, EB ;
BARTROLI, J ;
DOW, RL .
TETRAHEDRON LETTERS, 1986, 27 (41) :4957-4960
[5]   ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES [J].
EVANS, DA ;
BARTROLI, J ;
SHIH, TL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2127-2129
[6]   ASYMMETRIC ALKYLATION REACTIONS OF CHIRAL IMIDE ENOLATES - A PRACTICAL APPROACH TO THE ENANTIOSELECTIVE SYNTHESIS OF ALPHA-SUBSTITUTED CARBOXYLIC-ACID DERIVATIVES [J].
EVANS, DA ;
ENNIS, MD ;
MATHRE, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (06) :1737-1739
[7]   ON THE CHEMISTRY AND HIGH-FIELD NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY OF RAPAMYCIN [J].
FINDLAY, JA ;
RADICS, L .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1980, 58 (06) :579-590
[8]   STUDIES DIRECTED TOWARDS THE TOTAL SYNTHESIS OF FK-506 - PREPARATION OF A C(1) TO C(15) SEGMENT [J].
IRELAND, RE ;
WIPF, P .
TETRAHEDRON LETTERS, 1989, 30 (08) :919-922
[9]  
Johnson C.R., 1985, ALDRICHIM ACTA, V18, P3
[10]   UTILIZATION OF SULFOXIMINES AND DERIVATIVES AS REAGENTS FOR ORGANIC SYNTHESIS [J].
JOHNSON, CR .
ACCOUNTS OF CHEMICAL RESEARCH, 1973, 6 (10) :341-347