期刊
TETRAHEDRON LETTERS
卷 45, 期 31, 页码 6011-6015出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2004.06.036
关键词
N-acyliminium ion cyclization; diastereoselective synthesis; erythrinan alkaloids
A simple, three-step synthesis of 10b-substituted-hexahydropyrroloisoquinolines 12-17 starting from an L-tartaric acid derived imide is described. The methodology presented employs the addition of a Grignard reagent to the imide carbonyl group, followed by a one-pot acetylation-cyclization sequence. The crucial step, an acid-catalyzed carbon-carbon bond forming reaction via an N-acyliminium ion offers moderate to high stereoselectivity, which has been shown to be strongly dependent on the size of the R-substituent. The mixtures of pyrroloisoquinolines obtained can be separated as enantiomerically pure 2-silyloxy-derivatives. (C) 2004 Elsevier Ltd. All rights reserved.
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