期刊
TETRAHEDRON LETTERS
卷 49, 期 22, 页码 3592-3595出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.04.016
关键词
total synthesis; seco-psymberin; 'psymberate' side chain; (diacetoxyiodo) benzene; oxidative cyclization
The psymberin unsaturated 'psymberate' side chain 7 was synthesized in 7 steps (36% yield) with good diastereoselectivity using commercially available starting material to control the stereochemistry at C-4 and C-5. The synthesis of seco-psymberin was completed in an efficient manner based on a CuI mediated coupling reaction between vinyl iodide 8 and 'psymberamide' 7. In an attempt to synthesize natural psymberin from the seco-intermediate, a novel PhI(OAc)(2) mediated cascade ring closing reaction was discovered. A possible mechanistic pathway for the formation of the ring closing product was presented. (C) 2008 Elsevier Ltd. All rights reserved.
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