ORGN 394 |
Progress towards the total synthesis of Welwitindolinone A Isonitrile
| John L. Wood1, Sarah E. Reisman1, Joseph M. Ready2, Matthew M. Weiss1, and Makoto Hirata1. (1) Department of Chemistry, Yale University, Sterling Chemistry Laboratory, PO Box 208107, New Haven, CT 06520-8107, (2) University of Texas Southwestern Medical Center, Dallas, TX |
| Studies toward to total synthesis of the of the natural product Welwitindolinone A Isonitrile (4) have led to the development of a mild SmI2-mediated synthesis of spiro-oxindoles. Key intermediate 2 was prepared using a [2+2] cycloaddition to establish the bicyclo[4.2.0]octane core and a chlorine-induced semi-pinacol rearrangement to stereoselectively introduce the a-chloro quaternary center. SmI2-mediated intramolecular reductive cyclization of aryl isocyanate 2 resulted in the formation of highly functionalized spiro-oxindole 3 as a single diastereomer. 
|
| |
|
Total Synthesis, Process R&D, Combinatorial, Bioorganic, Physical Organic Chemistry
8:00 PM-10:00 PM, Tuesday, August 24, 2004 Pennsylvania Convention Center -- Hall D, Poster
Sci-Mix
8:00 PM-10:00 PM, Monday, August 23, 2004 Pennsylvania Convention Center -- Hall D, Sci-Mix
Division of Organic Chemistry
The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004
|