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First total synthesis of Combretastatin D-2 congeners named Isocorniculatolide A and 11-o-methylisocornicultolide
EP20412
Poster Title: First total synthesis of Combretastatin D-2 congeners named Isocorniculatolide A and 11-o-methylisocornicultolide
Submitted on 19 Dec 2013
Author(s): Vijaya Kumar.Tulam, Subhash Chandra Bose. Kotte, Sanjay Kumar. Hirasker, Prathama S Mainkar, P.M. Murali and K. Mukkanti.
Affiliations: JNTU Hyderabad
Poster Views: 2,556
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Poster Information
Abstract: First total synthesis of newly isolated natural products Isocorniculatolide A and 11-o-methylisocornicultolide A was accomplished. Commercially available 3, 4 dihydroxy benzaldehyde was selectively protected at the 4- position followed by the Wittig elongation to afford a, ß unsaturated ester which was subsequently treated with DIBAL to afford (E)-2-(benzyloxy)-5-(3-hydroxyprop-1-enyl) phenol and then finally coupled this intermediate with 3-(4-bromophenyl) propanoic acid to achieve (Z)-3-(4-(benzyloxy)-3-hydroxyphenyl) allyl 3-(4-bromophenyl) propanoate. Finally macro cyclization using Ullmann ether synthesis and then treatment with Pd/C accomplished Isocorculatolide A. In the same way we achieved 11-o-methylisocornicultolide starting from Isovanillin.Summary: As a part of our ongoing research in synthesizing the Biologically important Natural Products, here we are reporting First total synthesis of newly isolated isocorniculatolide A and 11-O-methyl corniculatolide A.Report abuse »
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