N-Methylative aziridine ring opening and asymmetric synthesis of MeBmt

被引:9
作者
Kim, Yongeun [1 ,2 ]
Yoon, Doo-Ha [1 ,2 ]
Ha, Hyun-Joon [1 ,2 ]
Kang, Kyung Yeon [3 ]
Lee, Won Koo [3 ]
机构
[1] Hankuk Univ Foreign Studies, Dept Chem, Yongin 449719, Kyunggi Do, South Korea
[2] Hankuk Univ Foreign Studies, Prot Res Ctr Bioind, Yongin 449719, Kyunggi Do, South Korea
[3] Sogang Univ, Dept Chem, Seoul 121742, South Korea
基金
新加坡国家研究基金会;
关键词
MeBmt; Asymmetric synthesis; Aziridine; Ring opening; Crotylation; UNUSUAL AMINO-ACID; STEREOSELECTIVE-SYNTHESIS; FORMAL SYNTHESIS; CHIRAL GLYCINE; CYCLOSPORINE; ALDEHYDES; KETONES;
D O I
10.1016/j.tetlet.2011.08.048
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Asymmetric synthesis of MeBmt, an unusual amino acid constituent of cyclosporine A, was achieved from aziridine-(2R)-carboxaldehyde through highly stereoselective addition of (E)-crotylboronate and the subsequent N-methylative aziridine ring opening as key steps. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5918 / 5920
页数:3
相关论文
共 33 条
[1]   A SHORT SYNTHESIS OF ENANTIOMERICALLY PURE (2S,3R,4R,6E)-3-HYDROXY-4-METHYL-2-(METHYLAMINO)-6-OCTENOIC ACID, THE UNUSUAL C-9 AMINO-ACID FOUND IN THE IMMUNOSUPPRESSIVE PEPTIDE CYCLOSPORINE [J].
AEBI, JD ;
DHAON, MK ;
RICH, DH .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (13) :2881-2886
[2]   A synthesis of herboxidiene [J].
Blakemore, PR ;
Kocienski, PJ ;
Morley, A ;
Muir, K .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (08) :955-968
[3]   A STEREOSELECTIVE SYNTHESIS OF MEBMT EMPLOYING A NEW CHIRAL GLYCINE ENOLATE DERIVATIVE [J].
BLASER, D ;
KO, SY ;
SEEBACH, D .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (21) :6230-6233
[4]   TRANSITION-METAL-PROMOTED HYDROBORATIONS OF ALKENES, EMERGING METHODOLOGY FOR ORGANIC TRANSFORMATIONS [J].
BURGESS, K ;
OHLMEYER, MJ .
CHEMICAL REVIEWS, 1991, 91 (06) :1179-1191
[5]   A formal synthesis of (-)-swainsonine from a chiral aziridine [J].
Choi, Hwan Geun ;
Kwon, Ji Hye ;
Kim, Jong Chan ;
Lee, Won Koo ;
Eum, Heesung ;
Ha, Hyun-Joon .
TETRAHEDRON LETTERS, 2010, 51 (25) :3284-3285
[6]   Stereoselective synthesis of MeBmt and methyl (4R,5S)-5-isopropyl-2-phenyloxazoline-4-carboxylate by a Pd-catalyzed equilibration [J].
Cook, GR ;
Shanker, PS .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (20) :6818-6822
[7]   Diastereoselective C-C bond formation at C-5 of vinyl sulfone-modified Hex-5-enofuranosyl carbohydrates: Diversity-oriented synthesis of branched-chain sugars and beyond [J].
Das, Indrajit ;
Pal, Tarun K. ;
Suresh, Cheravakkattu G. ;
Pathak, Tanmaya .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (15) :5523-5533
[8]   CYCLOSPORIN-A AND C NEW METABOLITES FROM TRICHODERMA-POLYSPORUM (LINK EX PERS) RIFAI [J].
DREYFUSS, M ;
HARRI, E ;
HOFMANN, H ;
KOBEL, H ;
PACHE, W ;
TSCHERTER, H .
EUROPEAN JOURNAL OF APPLIED MICROBIOLOGY, 1976, 3 (02) :125-133
[9]   ASYMMETRIC GLYCINE ENOLATE ALDOL REACTIONS - SYNTHESIS OF CYCLOSPORINES UNUSUAL AMINO-ACID, MEBMT [J].
EVANS, DA ;
WEBER, AE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (21) :6757-6761
[10]   CYCLOSPORINE - A REVIEW OF ITS PHARMACODYNAMIC AND PHARMACOKINETIC PROPERTIES, AND THERAPEUTIC USE IN IMMUNOREGULATORY DISORDERS [J].
FAULDS, D ;
GOA, KL ;
BENFIELD, P .
DRUGS, 1993, 45 (06) :953-1040