Journal
TETRAHEDRON
Volume 64, Issue 13, Pages 2924-2929Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.01.101
Keywords
clavine alkaloids; (+/-)-cycloclavine; total synthesis from 4-bromo-Uhle's ketone; modified intramolecular Reformatsky-type cyclization; cyclopropanation with diazomethane
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Starting from 4-bromo-Uhle's ketone (2), an alkylation step using ethyl 3-methylamino-propionate followed by intramolecular aldol condensation in two steps, transformation of the ester group into a methyl group, and finally cyclopropanation of the 8,9 double bond, resulted in a six-step total synthesis of (+/-)-cycloclavine (1). (C) 2008 Elsevier Ltd. All rights reserved.
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