Stereodivergent approach to both syn- and anti-isomers of γ-amino-β-hydroxy acids: (3S,4S)- and (3R,4S)-AHPPA derivatives

被引：6

作者：

Yoo, Dongwon ^{[1
]}

Song, Jeeyun ^{[1
]}

Kang, Moon Sung ^{[1
]}

Kang, Eun-Sil ^{[1
]}

Kim, Young Gyu ^{[1
]}

机构：

[1] Seoul Natl Univ, Dept Chem & Biol Engn, Seoul 151744, South Korea

来源：

TETRAHEDRON-ASYMMETRY | 2011年 / 22卷 / 16-17期

关键词：

RESISTANCE-REVERSING ACTIVITY; ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; EFFICIENT SYNTHESIS; PROTEASE INHIBITOR; 4-AMINO-3-HYDROXY-5-PHENYLPENTANOIC ACID; STEREOSPECIFIC SYNTHESIS; CYCLIC DEPSIPEPTIDE; TETRAMIC ACID; TASIAMIDE-B;

D O I：

10.1016/j.tetasy.2011.09.021

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A stereodivergent approach employing an N-hydroxymethyl group has been utilized to produce both diastereomeric derivatives of (3S,4S)-AHPPA 3 and (312,4S)-AHPPA 4, via an intramolecular conjugate addition and an intramolecular epoxidation, respectively. The selectivity of the intramolecular conjugate addition was more than 10:1 while that of the intramolecular epoxidation was more than 1:20. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：1700 / 1704

页数：5

共 36 条

[1] A synthetic approach to 3-hydroxy 4-substituted carboxylic acids based on the stereoselective reduction of 1-trimethyisilyl-1-alkyn-3-ones [J].

Alemany, C ;

Bach, J ;

Garcia, J ;

López, M ;

Rodríguez, AB .

TETRAHEDRON, 2000, 56 (47) :9305-9312

[2] A totally stereocontrolled route to N-methyl-γ-amino-β-hydroxy acids:: Asymmetric synthesis of the amino acid component of hapalosin [J].

Catasús, M ;

Moyano, A ;

Pericàs, MA ;

Riera, A .

TETRAHEDRON LETTERS, 1999, 40 (52) :9309-9312

[3] Palladium-catalyzed formation and stereoselective isomerization of 5-vinyloxazolines. Application to the formal synthesis of (S,S)-4-amino-3-hydroxy-5-phenylpentanoic acid [J].

Cook, GR ;

Shanker, PS .

TETRAHEDRON LETTERS, 1998, 39 (21) :3405-3408

[4] Diversity-oriented asymmetric synthesis of hapalosin: Construction of three small C9/C4/C3-modified hapalosin analogue libraries [J].

Dai, Chao-Feng ;

Cheng, Fang ;

Xu, Hai-Chao ;

Ruan, Yuan-Ping ;

Huang, Pei-Qiang .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2007, 9 (03) :386-394

[5] A NOVEL SHORT AND EFFICIENT ASYMMETRIC-SYNTHESIS OF STATINE ANALOGS [J].

DEVANT, RM ;

RADUNZ, HE .

TETRAHEDRON LETTERS, 1988, 29 (19) :2307-2310

[6]

GHOSH AK, 1996, Z ANGEW CHEM INT ED, V35, P74

[7]

Haddad M, 1999, SYNLETT, P1118

[8] Synthesis of Chiral Amines Using α-Amino Aldehydes [J].

Hili, Ryan ;

Baktharaman, Sivaraj ;

Yudin, Andrei K. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (31) :5201-5213

[9] A flexible approach to (S)-5-alkyl tetramic acid derivatives:: Application to the asymmetric synthesis of (+)-preussin and protected (3S,4S)-AHPPA [J].

Huang, PQ ;

Wu, TJ ;

Ruan, YP .

ORGANIC LETTERS, 2003, 5 (23) :4341-4344

[10] N-hydroxymethyl group for configurationally stable N-alkoxycarbonyl α-amino aldehydes [J].

Hyun, SI ;

Kim, YG .

TETRAHEDRON LETTERS, 1998, 39 (24) :4299-4302

← 1 2 3 4 →