A new route to optically pure highly functionalized tetrahydro-isoquinolines with a quaternary carbon stereocenter

作者：Kaluza Zbigniew^*; Mostowicz Danuta; Dolega Grzegorz; Wojcik Robert

来源：Tetrahedron, 2008, 64(10): 2321-2328.

DOI：10.1016/j.tet.2008.01.011

• stereoselective synthesis
• isoquinoline alkaloids
• Canizzaro reaction

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 beta-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.

• 出版日期2008-3-3