SYNTHESIS OF THE C20-C34 SEGMENT OF THE IMMUNOSUPPRESSANT FK-506 VIA STEREOCONTROLLED ALDOL COUPLING - APPLICATION OF A REMOTE CHELATION EFFECT

被引：0
作者：
WHITE, JD
TOSKE, SG
YAKURA, T
机构：
来源：
SYNLETT | 1994年 / 08期
关键词：
(-)-QUINIC ACID; Z-CROTYLBORONATE; ASYMMETRIC ALDOL; FELKIN ADDITION; CHELATED ENOLATE;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Stereoselective aldol condensation of an alpha-chiral methyl ketone, prepared from ethyl (R)-3-hydroxybutyrate, with an alpha-chiral aldehyde, prepared from (-)-quinic acid, was used to construct the C20-C34 segment of the immunosuppressant FK-506. Stereoselection in this process is attributed to tight coordination of the lithium enolate with a beta-trityl ether thereby imparting a large steric bias to the ketone enolate.
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页码：591 / 593
页数：3
相关论文
共 57 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]   RADICAL-INDUCED RING-OPENING OF EPOXIDES - A CONVENIENT ALTERNATIVE TO THE WHARTON REARRANGEMENT [J].
BARTON, DHR ;
MOTHERWELL, RSH ;
MOTHERWELL, WB .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (08) :2363-2367
[3]  
CHAUDHARY SK, 1979, TETRAHEDRON LETT, P95
[4]   ENANTIOSELECTIVE SYNTHESIS OF THE C(18)-C(35) SEGMENT OF IMMUNOSUPPRESSANT FK-506 USING EFFICIENT NEW METHODOLOGY [J].
COREY, EJ ;
HUANG, HC .
TETRAHEDRON LETTERS, 1989, 30 (39) :5235-5238
[5]  
DEPOOTER H, 1975, B SOC CHIM BELG, V84, P835
[6]   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
[7]   SYNTHETIC ROUTE TO THE TRICARBONYL REGION OF FK-506 [J].
EGBERTSON, M ;
DANISHEFSKY, SJ .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (01) :11-12
[8]   ABOUT THE STEREOSPECIFIC ALPHA-ALKYLATION OF BETA-HYDROXYESTERS [J].
FRATER, G .
HELVETICA CHIMICA ACTA, 1979, 62 (08) :2825-2828
[9]   STUDIES RELATING TO THE IMMUNOSUPPRESSIVE ACTIVITY OF FK506 [J].
FURBER, M ;
COOPER, ME ;
DONALD, DK .
TETRAHEDRON LETTERS, 1993, 34 (08) :1351-1354
[10]   A CHEMOENZYMATIC SYNTHESIS OF THE C-10-C-19 MOIETY OF FK506 [J].
GU, RL ;
SIH, CJ .
TETRAHEDRON LETTERS, 1990, 31 (23) :3283-3286
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