Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5224468 | Tetrahedron | 2008 | 8 Pages |
Abstract
A facile synthesis of highly substituted, optically pure tetrahydro-isoquinolines with a quaternary carbon stereocenter is described. Glycolic cleavage of 1,2-dihydroxy-hexahydro-pyrrolo-isoquinolines 1 affords a mixture of cyclic hemiacetals, which can be converted via intramolecular chemoselective Cannizzaro reaction into respective β-amino alcohols, whereas the IBX oxidation gives N-formyl aldehydes. We have demonstrated the utility of such synthons by the synthesis of (+)-6,7-dimethoxy-salsoline-1-carboxylic acid and its new 1-phenyl analogue.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Zbigniew KaÅuża, Danuta Mostowicz, Grzegorz DoÅÄga, Robert Wójcik,