Asymmetric synthesis of (2S,3R)-capreomycidine and the total synthesis of capreomycin IB

被引：58

作者：

DeMong, DE ^{[1
]}

Williams, RM ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 28期

关键词：

D O I：

10.1021/ja0351241

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A 27 step total synthesis of the tuberculostatic macrocyclic peptide antibiotic capreomycin 113 has been accomplished. The synthesis features the use of an enolate-aldimine condensation between a chiral glycine aluminum enolate and the benzyl imine of 3-tert-butyldimethylsiloxy-propanal as a means of preparing the cyclic guanidine amino acid (2S,3R)-capreomycidine. Additionally, a Hofmann rearrangement was exacted on a late-stage pentapeptide in order to transform an asparagine residue into a diaminopropanoic acid residue.

引用

下载

页码：8561 / 8565

页数：5

共 50 条

[41] Diastereoselective synthesis of (2S*,3R*)- and (2R*,3R*)-2,6-dimethyl-2-homoprenyl-chroman-3-ol
Inoue, S
Asami, M
Honda, K
Shrestha, KS
Takahashi, M
Yoshino, T
SYNLETT, 1998, (06) : 679 - +
[42] SYNTHESIS OF (2R,3R)-, (2S,3S)-, (2R,3S)- AND (2S,3R)-IMIDAZOLE GLYCEROL PHOSPHATES (IGP) - SUBSTRATES FOR IGP-DEHYDRATASE (IGPD)
SAIKA, H
FRUH, T
IWASAKI, G
KOIZUMI, S
MORI, I
HAYAKAWA, K
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (10) : 2129 - 2134
[43] Asymmetric conjugate reductions with samarium diiodide:: asymmetric synthesis of (2S,3R)- and (2S,3S)[2-2H,3-2H]-leucine-(S)-phenylalanine dipeptides and (2S,3R)[2-2H,3-2H]-phenylalanine methyl ester
Davies, SG
Rodríguez-Sola, H
Tamayo, JA
Cowley, AR
Concellón, C
Garner, AC
Parkes, AL
Smith, AD
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (08) : 1435 - 1447
[44] Asymmetric synthesis of (1R,2S,3R)-3-methylcispentacin and (1S,2S,3R)-3-methyltranspentacin by kinetic resolution of tert-butyl (±)-3-methylcyclopentene-1-carboxylate
Bunnage, ME
Chippindale, AM
Davies, SG
Parkin, RM
Smith, AD
Withey, JM
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (21) : 3698 - 3707
[45] Asymmetric total synthesis of (2S,3S)-3-hydroxypipecolic acid
Chavan, Subhash P.
Dumare, Nilesh B.
Harale, Kishor R.
Kalkote, Uttam R.
TETRAHEDRON LETTERS, 2011, 52 (03) : 404 - 406
[46] SYNTHESIS OF ENANTIOMERICALLY PURE AND COMPATIBLY PROTECTED (2S,3R)-DIAMINOBUTYRIC AND (2S,3S)-DIAMINOBUTYRIC ACIDS
SCHMIDT, U
MUNDINGER, K
RIEDL, B
HAAS, G
LAU, R
SYNTHESIS-STUTTGART, 1992, (12): : 1201 - 1202
[47] Asymmetric synthesis of (1R,2S,3R)-2-acetyl-5-(1,2,3,4-tetrahydroxybutyl)thiazole
Ung, AT
Pyne, SG
Skelton, BW
White, AH
TETRAHEDRON, 1996, 52 (44) : 14069 - 14078
[48] Asymmetric synthesis of (1R,2S,3R)-2-acetyl-4-(1,2,3,4-tetrahydroxybutyl)thiazole
Ung, AT
Pyne, SG
TETRAHEDRON-ASYMMETRY, 1998, 9 (08) : 1395 - 1407
[49] Asymmetric synthesis of (1R,2S,3R)-2-acetyl-4-(1,2,3,4-tetrahydroxybutyl) thiazole
Tetrahedron Asymmetry, 8 (1395):
[50] Synthesis of (2S,3R)-β-methyltyrosine catalyzed by tyrosine phenol-lyase
Kim, K
Cole, PA
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (08) : 1205 - 1208

← 1 2 3 4 5 →