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The Laulimalide Family: Total Synthesis and Biological Evaluation of Neolaulimalide,Isolaulimalide, Laulimalide and a Nonnatural Analogue
Authors:Andreas Gollner Dipl‐Ing  Karl‐Heinz Altmann Prof?Dr  Jürg Gertsch Dr  Johann Mulzer Prof?Dr
Institution:1. University of Vienna, Institute of Organic Chemistry, W?hringerstrasse 38, 1090 Vienna (Austria), Fax: (+43)?1‐4277‐52189, Homepage: http://www.univie.ac.at/rg_mulzer/;2. ETH Zürich, Institut f. Pharmazeut. Wissenschaften, HCI H 405, Wolfgang‐Pauli‐Strasse 10, 8093 Zürich (Switzerland)
Abstract:A sensitive family : The first total synthesis of the antitumor agents neolaulimalide and isolaulimalide as well as a highly efficient route to laulimalide is described. A Kulinkovich reaction followed by a cyclopropyl–allyl rearrangement is used to install the exo‐methylene group. The cytotoxicity of neolaulimalide could be confirmed for the first time since its original isolation and it could be shown that it induces tubulin polymerization as efficiently as laulimalide.
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Keywords:acyl migration  antitumor agents  natural products  olefination  total synthesis
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