Journal
TETRAHEDRON
Volume 62, Issue 51, Pages 12011-12016Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2006.09.079
Keywords
19-hydroxy-ibophyllidine; 19-hydroxy-20-epiibophyllidine; indole alkaloids; natural products
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Starting from methyl-5-oxohexanoate we produced the appropriately functionalized aldehyde, which, after having been allowed to react with the tryptamine derivative in a [4+2] cycloaddition reaction as the final step, yielded the molecule containing a D-seco-aspido-spermane skeleton. From the latter we could successfully produce a 1: 1 mixture of protected epimers, the desilylation reaction of the protected molecules gave the alkaloids (+/-)-19-hydroxy-ibophyllidine and (+/-)-19-hydroxy-20-epiibophyllidine in good yield. (c) 2006 Elsevier Ltd. All rights reserved.
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