Journal
TETRAHEDRON
Volume 63, Issue 35, Pages 8499-8513Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2007.05.127
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The first total synthesis of the structurally novel cyclotryptophan alkaloid asperazine is reported. The central step in the synthetic sequence is a diastereoselective intramolecular Heck reaction in which the substituent controlling stereoselection is external to the ring being formed. This synthesis confirmed the structure of (+)- asperazine (1) proposed by Crews and co- workers and provided material for additional biological studies. The in vitro cytotoxicity originally reported for the marine isolate was not confirmed with synthetic (+)- asperazine. (c) 2007 Elsevier Ltd. All rights reserved.
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