A NEW, VERSATILE AND STEREOSPECIFIC ROUTE TO UNUSUAL AMINO-ACIDS - THE ENANTIOSPECIFIC TOTAL SYNTHESIS OF STATINE AMIDE AND ITS 3 STEREOISOMERS

被引：23

作者：

BESSODES, M

SAIAH, M

ANTONAKIS, K

机构：

[1] Institut de Recherches Scientifiques sur le Cancer, Villejuif Cedex

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 16期

关键词：

D O I：

10.1021/jo00042a026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Total syntheses of statine amide [(3S,4S)-4-amino-3-hydroxy-6-methylheptanamide] and its three stereoisomers are described in order to illustrate the versatility of a new route to beta-hydroxy-gamma-amino acids. The enantioselective Sharpless epoxidation of a racemic allylic alcohol is used to generate chiral intermediates. The allylic alcohol, 3-hydroxy-5-methyl-1-hexene, can be prepared in at least two different ways from readily available materials. The methodology that is described should prove applicable to the synthesis of other analogues of statine.

引用

页码：4441 / 4444

页数：4

共 34 条

[1] STEREOSELECTIVE SYNTHESIS OF STATIN ANALOGS
BERNARDI, A
MICHELI, F
POTENZA, D
SCOLASTICO, C
VILLA, R
[J]. TETRAHEDRON LETTERS, 1990, 31 (34) : 4949 - 4952
[2] RENIN INHIBITORS - SYNTHESES OF SUBNANOMOLAR, COMPETITIVE, TRANSITION-STATE ANALOG INHIBITORS CONTAINING A NOVEL ANALOG OF STATINE
BOGER, J
PAYNE, LS
PERLOW, DS
LOHR, NS
POE, M
BLAINE, EH
ULM, EH
SCHORN, TW
LAMONT, BI
LIN, TY
KAWAI, M
RICH, DH
VEBER, DF
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (12) : 1779 - 1790
[3] CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION
GAO, Y
HANSON, RM
KLUNDER, JM
KO, SY
MASAMUNE, H
SHARPLESS, KB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) : 5765 - 5780
[4] SYNTHETIC STUDIES OF DIDEMNINS .2. APPROACHES TO STATINE DIASTEREOMERS
HARRIS, BD
BHAT, KL
JOULLIE, MM
[J]. TETRAHEDRON LETTERS, 1987, 28 (25) : 2837 - 2840
[5] A NEW FACILE DIASTEREOCONVERSION OF 2-AMINO ALCOHOLS INVOLVING A NOVEL CYCLOCARBAMATION
KANO, S
YOKOMATSU, T
IWASAWA, H
SHIBUYA, S
[J]. TETRAHEDRON LETTERS, 1987, 28 (50) : 6331 - 6334
[6] HIGHLY STEREOCONTROLLED SYNTHESIS OF THE 4 INDIVIDUAL STEREOISOMERS OF STATINE
KANO, S
YUASA, Y
YOKOMATSU, T
SHIBUYA, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (16) : 3865 - 3868
[7] THE 1ST PRACTICAL METHOD FOR ASYMMETRIC EPOXIDATION
KATSUKI, T
SHARPLESS, KB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) : 5974 - 5976
[8] NOVEL SYNTHESIS OF (2S, 3R, 4S)-4-AMINO-5-CYCLOHEXYL-1-MORPHOLINO-2,3-PENTANEDIOL AND (2S, 3R, 4S)-2-AMINO-1-CYCLOHEXYL-6-METHYL-3,4-HEPTANEDIOL, THE C-TERMINAL COMPONENTS OF RENIN INHIBITORS
KOBAYASHI, Y
NAKATANI, K
ITO, Y
TERASHIMA, S
[J]. CHEMISTRY LETTERS, 1990, (09) : 1709 - 1710
[9] KOGEN H, 1987, J CHEM SOC CHEM COMM, P311
[10] SYNTHESIS OF STATINE FROM (S)-MALIC ACID - STEREOCONTROL VIA RADICAL CYCLIZATION
KOOT, WJ
VANGINKEL, R
KRANENBURG, M
HIEMSTRA, H
LOUWRIER, S
MOOLENAAR, MJ
SPECKAMP, WN
[J]. TETRAHEDRON LETTERS, 1991, 32 (03) : 401 - 404

← 1 2 3 4 →