TOTAL SYNTHESES OF CLOSE ANALOGS OF THE IMMUNOSUPPRESSANT FK506

被引:20
作者
BATCHELOR, MJ
GILLESPIE, RJ
GOLEC, JMC
HEDGECOCK, CJR
JONES, SD
MURDOCH, R
机构
[1] Roussel Laboratories Ltd, Swindon, Wiltshire SN3 5BZ England, Kingfisher Drive, Covingham
关键词
D O I
10.1016/S0040-4020(01)80796-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The total synthesis of an analogue of FK506, in which the substituted cyclohexyl residue at C-28 has been replaced by a phenyl group, is described. This synthesis demonstrates (i) the successful application of new methodology for the introduction of the masked tricarbonyl grouping (C-8-C-10), and(ii) new synthetic routes to the (C-10-C-19) and (C-22-C-26) regions.
引用
收藏
页码:809 / 826
页数:18
相关论文
共 27 条
[1]  
AHMED S, 1986, TETRAHEDRON LETT, V27, P3791
[2]  
BASHA A, 1977, TETRAHEDRON LETT, P4171
[3]   A NOVEL APPLICATION OF THE DESS-MARTIN REAGENT TO THE SYNTHESIS OF AN FK506 ANALOG AND OTHER TRICARBONYL COMPOUNDS [J].
BATCHELOR, MJ ;
GILLESPIE, RJ ;
GOLEC, JMC ;
HEDGECOCK, CJR .
TETRAHEDRON LETTERS, 1993, 34 (01) :167-170
[4]   1,3-SYN DIASTEREOSELECTIVE REDUCTION OF BETA-HYDROXYKETONES UTILIZING ALKOXYDIALKYLBORANES [J].
CHEN, KM ;
HARDTMANN, GE ;
PRASAD, K ;
REPIC, O ;
SHAPIRO, MJ .
TETRAHEDRON LETTERS, 1987, 28 (02) :155-158
[5]   PRACTICAL ENANTIOSELECTIVE DIELS-ALDER AND ALDOL REACTIONS USING A NEW CHIRAL CONTROLLER SYSTEM [J].
COREY, EJ ;
IMWINKELRIED, R ;
PIKUL, S ;
XIANG, YB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) :5493-5495
[7]   A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287
[8]  
DEYO DT, 1988, SYNTHESIS-STUTTGART, P608
[9]   DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE [J].
EVANS, DA ;
CHAPMAN, KT ;
CARREIRA, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3560-3578
[10]   TOTAL SYNTHESIS OF THE IONOPHORE ANTIBIOTIC X-206 - STUDIES RELEVANT TO THE STEREOSELECTIVE SYNTHESIS OF THE C(17)-C(26) SYNTHON [J].
EVANS, DA ;
BENDER, SL .
TETRAHEDRON LETTERS, 1986, 27 (07) :799-802