Access to the cis-Fused Stereoisomers of Proline Analogues Containing an Octahydroindole Core

被引：33

作者：

Sayago, Francisco J. ^{[1
]}

Laborda, Pedro ^{[1
]}

Isabel Calaza, M. ^{[1
]}

Jimenez, Ana I. ^{[1
]}

Cativiela, Carlos ^{[1
]}

机构：

[1] Univ Zaragoza, Dept Quim Organ, Inst Ciencia Mat Aragon, CSIC, E-50009 Zaragoza, Spain

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 11期

关键词：

Amino acids; Asymmetric synthesis; Diastereoselectivity; Chiral resolution; CONVERTING ENZYME-INHIBITORS; CATALYTIC ASYMMETRIC HYDROGENATION; BRADYKININ ANTAGONIST DIMER; CHIRAL STATIONARY PHASES; CONSTRAINED AMINO-ACIDS; CANCER CELL-LINES; STEREOSELECTIVE-SYNTHESIS; IN-VITRO; EFFICIENT RESOLUTION; THERAPEUTIC PEPTIDES;

D O I：

10.1002/ejoc.201001710

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An overview of the synthetic methods developed to build all the cis-fused stereoisomers of octahydroindole-2-carboxylic acid and its alpha-methylated derivative in enantiomerically pure form is presented. Both asymmetric synthetic strategies (auxiliary-or substrate-controlled processes) and procedures based on the resolution of racemic compounds (chemical, enzymatic, and chromatographic processes) are summarized. Special emphasis has been placed on those strategies able to provide multigram quantities of enantiopure compounds, a prerequisite to make downstream biological applications feasible.

引用

页码：2011 / 2028

页数：18

共 17 条

[1] Stereodivergent Synthesis of Two Novel α-Aminophosphonic Acids Characterised by a cis-Fused Octahydroindole System
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[4] Hexafluoroisopropanol: a powerful solvent for the hydrogenation of indole derivatives. Selective access to tetrahydroindoles or cis-fused octahydroindoles
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[6] SYNTHESIS OF ALL STEREOISOMERS OF EUDESM-11-EN-4-OL .1. STEREOSPECIFIC SYNTHESIS OF THE TRANS-FUSED AND CIS-FUSED OCTAHYDRO-8-HYDROXY-4A,8-DIMETHYL-2(1H)-NAPHTHALENONES - CONFORMATIONAL-ANALYSIS OF THE CIS-FUSED COMPOUNDS
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[8] Bismuth(III) Chloride Catalyzed Intramolecular Hetero-Diels-Alder Reaction: Access to cis-Fused Angular Hexahydrobenzo[c]acridines
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