Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 11, Pages 2011-2028Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201001710
Keywords
Amino acids; Asymmetric synthesis; Diastereoselectivity; Chiral resolution
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Funding
- Ministerio de Ciencia e Innovacion [CTQ2007-62245, CTQ2010-17436]
- Gobierno de Aragon [PIP206/2005, E40]
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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.
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