期刊
TETRAHEDRON
卷 64, 期 10, 页码 2321-2328出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.01.011
关键词
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. (C) 2008 Elsevier Ltd. All rights reserved.
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