A versatile approach to the activated form of (3S, 4R)-statine and its analogues

被引:13
作者
Huang, PQ [1 ]
Ye, JL
Chen, Z
Ruan, YP
Gao, JX
机构
[1] Xiamen Univ, Dept Chem, Xiamen 361005, Peoples R China
[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1080/00397919808005095
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A concise and versatile approach to the activated form of(3S, 4R)-statine 6 and its analogues is described. The key steps involve reductive alkylation of (S)-O-tert-butyldimethysilylmalimide 12.
引用
收藏
页码:417 / 426
页数:10
相关论文
共 23 条
[11]   First asymmetric synthesis of (2R,3R)-3-amino-1-benzyl-2-methylpyrrolidine via a highly diastereoselective reductive alkylation [J].
Huang, PQ ;
Wang, SL ;
Zheng, H ;
Fei, XS .
TETRAHEDRON LETTERS, 1997, 38 (02) :271-272
[12]   STEREOSPECIFIC SYNTHESIS OF S,S-STATINE AND ITS CONGENERS [J].
KLUTCHKO, S ;
OBRIEN, P ;
HODGES, JC .
SYNTHETIC COMMUNICATIONS, 1989, 19 (13-14) :2573-2583
[13]   SYNTHESIS OF STATINE FROM (S)-MALIC ACID - STEREOCONTROL VIA RADICAL CYCLIZATION [J].
KOOT, WJ ;
VANGINKEL, R ;
KRANENBURG, M ;
HIEMSTRA, H ;
LOUWRIER, S ;
MOOLENAAR, MJ ;
SPECKAMP, WN .
TETRAHEDRON LETTERS, 1991, 32 (03) :401-404
[14]  
KURSANOV DN, 1974, SYNTHESIS-STUTTGART, P633
[15]  
Ma DW, 1996, TETRAHEDRON-ASYMMETR, V7, P2365
[16]   Novel enantioselective approach to gamma-lactams from chiral enol ethers: Synthesis of (-)-statine [J].
Nebois, P ;
Greene, AE .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) :5210-5211
[17]   New approach to the coupling of gamma-amino beta-hydroxy acids and beta,gamma-dihydroxy acids with alpha-amino acid esters [J].
Palomo, C ;
Miranda, JI ;
Linden, A .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9196-9201
[18]   SYNTHESIS OF (3S,4S)-4-AMINO-3-HYDROXY-6-METHYLHEPTANOIC ACID-DERIVATIVES - ANALYSIS OF DIASTEREOMERIC PURITY [J].
RICH, DH ;
SUN, ET ;
BOPARAI, AS .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (18) :3624-3626
[19]   SYNTHESIS OF ANALOGS OF THE CARBOXYL PROTEASE INHIBITOR PEPSTATIN - EFFECT OF STRUCTURE ON INHIBITION OF PEPSIN AND RENIN [J].
RICH, DH ;
SUN, ETO ;
ULM, E .
JOURNAL OF MEDICINAL CHEMISTRY, 1980, 23 (01) :27-33
[20]   TOTAL SYNTHESIS OF DIDEMNIN-A, DIDEMNIN-B, AND DIDEMNIN-C [J].
RINEHART, KL ;
KISHORE, V ;
NAGARAJAN, S ;
LAKE, RJ ;
GLOER, JB ;
BOZICH, FA ;
LI, KM ;
MALECZKA, RE ;
TODSEN, WL ;
MUNRO, MHG ;
SULLINS, DW ;
SAKAI, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (22) :6846-6848