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
[11]  
Hiemstra H., 1991, COMPREHENSIVE ORGANI, V2, P1047
[12]  
HOREAU S, 1996, TETRAHEDRON-ASYMMETR, V7, P2585
[13]  
Kondo Y., 1957, J SERICULT SCI JAPAN, V26, P345
[14]   Allenylmethylsilanes as nucleophiles in N-acyliminium ion chemistry [J].
Mentink, G ;
van Maarseveen, JH ;
Hiemstra, H .
ORGANIC LETTERS, 2002, 4 (20) :3497-3500
[15]   New and efficient synthesis of azabicyclo[4.4.0]alkane amino acids by Rh-catalyzed cyclohydrocarbonylation [J].
Mizutani, N ;
Chiou, WH ;
Ojima, I .
ORGANIC LETTERS, 2002, 4 (26) :4575-4578
[16]   Efficient synthesis of piperidine derivatives. Development of metal triflate-catalyzed diastereoselective nucleophilic substitution reactions of 2-methoxy- and 2-acyloxypiperidines [J].
Okitsu, O ;
Suzuki, R ;
Kobayashi, S .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (03) :809-823
[17]   Transformation in carbohydrate chemistry, Part 5. An efficient one step dihydroxylation of 1,2-glycals with oxone in acetone [J].
Rani, S ;
Vankar, YD .
TETRAHEDRON LETTERS, 2003, 44 (05) :907-909
[18]   PEPTIDOMIMETIC SYNTHESIS - UTILIZATION OF N-ACYLIMINIUM ION CYCLIZATION CHEMISTRY IN THE GENERATION OF 7,6-FUSED AND 7,5-FUSED BICYCLIC LACTAMS [J].
ROBL, JA .
TETRAHEDRON LETTERS, 1994, 35 (03) :393-396
[19]   CHEMICAL SYNTHESIS OF ALLYSINE ETHYLENE ACETAL AND CONVERSION IN-SITU INTO 1-PIPERIDEINE-6-CARBOXYLIC ACID - KEY INTERMEDIATE OF THE ALPHA-AMINOADIPIC ACID FOR BETA-LACTAM ANTIBIOTICS BIOSYNTHESIS [J].
RUMBERO, A ;
MARTIN, JF ;
LUMBRERAS, MA ;
LIRAS, P ;
ESMAHAN, C .
BIOORGANIC & MEDICINAL CHEMISTRY, 1995, 3 (09) :1237-1240
[20]  
Santos LS, 2002, SYNTHESIS-STUTTGART, P87
123