Journal
TETRAHEDRON
Volume 61, Issue 30, Pages 7211-7218Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2005.05.038
Keywords
total synthesis; bastadin; oxidative coupling; angiogenesis; marine sponge
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An efficient total synthesis of bastadin 6 (1), a cyclic tetramer of brominated tyrosine derivatives from the marine sponge, lanthella basta, with selective anti-angiogenic activity, was accomplished. We developed a novel Ce(IV)-mediated oxidative coupling reaction of 2,6-dibromophenols to give the diaryl ether derivatives, the characteristic segment of 1. Condensation of two segments and subsequent intramolecular macrocyclization gave bastadin 6 (1) in nine steps, 26% overall yield. (c) 2005 Elsevier Ltd. All rights reserved.
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