Diastereoselective synthesis of (2S,5R)-5-hydroxypipecolic acid and 6-substituted derivatives

被引：39
作者：
Botman, PNM
Dommerholt, FJ
de Gelder, R
Broxterman, QB
Schoemaker, HE
Rutjes, FPJT
Blaauw, RH
机构：
[1] Chiralix BV, NL-6503 CB Nijmegen, Netherlands
[2] Radbound Univ, IMM, NL-6525 ED Nijmegen, Netherlands
[3] DSM Res BV, Life Sci Adv Synt Catalysis & Dev, NL-6160 MD Geleen, Netherlands
来源：
ORGANIC LETTERS | 2004年 / 6卷 / 26期
关键词：
D O I：
10.1021/ol047774v
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein, we report a diastereoselective synthesis of the natural product (2S,5R)-5-hydroxypipecolic acid and 6-substituted derivatives thereof. The key step in the synthetic sequence is a novel highly diastereoselective epoxidation reaction of an enantiomerically pure cyclic enamide intermediate.
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页码：4941 / 4944
页数：4
相关论文
共 29 条
[1]   CHIRAL SYNTHESIS OF 5-HYDROXY-(L)-PIPECOLIC ACIDS FROM (L)-GLUTAMIC ACID [J].
BAILEY, PD ;
BRYANS, JS .
TETRAHEDRON LETTERS, 1988, 29 (18) :2231-2234
[2]  
BOESTEN WHJ, 1999, Patent No. [0905257, 905257]
[3]   A chiral relay auxiliary for the synthesis of homochiral α-amino acids [J].
Bull, SD ;
Davies, SG ;
Epstein, SW ;
Leech, MA ;
Ouzman, JVA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (15) :2321-2330
[4]   Synthesis of the angiotensin-converting enzyme inhibitors (-)-A58365A and (-)-A58365B from a common intermediate [J].
Clive, DLJ ;
Coltart, DM ;
Zhou, YX .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (05) :1447-1454
[5]   L-CIS-5-HYDROXYPIPECOLIC ACID FROM SEEDS OF GYMNOCLADUS-DIOICUS [J].
DESPONTIN, J ;
MARLIER, M ;
DARDENNE, G .
PHYTOCHEMISTRY, 1977, 16 (03) :387-388
[6]  
FOWDEN L., 1970, Progress in phytochemistry, V2, P203
[7]  
GOAS G, 1970, CR ACAD SCI D NAT, V271, P1368
[8]  
Hatanaka, 1972, SCI PAP COLL GEN ED, V22, P117
[9]   SYNTHESIS OF 2S,5S-AND 2R,5S-5-HYDROXYPIPECOLIC ACID VIA AMIDE-METHYLENATION OF S-5-HYDROXY-2-PIPERIDONE WITH DIMETHYLTITANOCENE [J].
HERDEIS, C ;
HELLER, E .
TETRAHEDRON-ASYMMETRY, 1993, 4 (09) :2085-2094
[10]   PIPECOLIC ACIDS .3. SYNTHESIS OF UNNATURAL 2R,5S-5-HYDROXYPIPECOLIC ACID VIA HOMOCHIRAL ACYLIMINIUM ION [J].
HERDEIS, C ;
ENGEL, W .
TETRAHEDRON-ASYMMETRY, 1991, 2 (10) :945-948
123