Scope and limitations of the Mukaiyama oxidative cyclization of bis-homoallylic alcohols

CHED 438

Danielle Porras, dporras@stedwards.edu1, Jeffrey S. T. Gorman, jeffreyg@stedwards.edu1, and Brian L. Pagenkopf2. (1) Department of Chemistry, St. Edward's University, 3001 S. Congress Ave., Austin, TX 78704, (2) Department of Chemistry, The University of Western Ontario, London, ON N6A 5B7, Canada
The cobalt-mediated oxidative cyclization of bis-homoallylic alcohols introduced by Mukaiyama has provided an extremely efficient route to trans-2,5-disubstituted tetrahydrofurans (THF's). The method has been elegantly applied to total syntheses of acetogenins such as bullatacin and mucocin and, more recently, to the synthesis of aplysiallene. In the current work, the scope and limitations of this oxidative cyclization of are presented with a focus on the effects of other substitution patterns on reaction efficiency and stereochemical outcomes.
 

Undergraduate Research Poster Session: Organic Chemistry
11:00 AM-1:00 PM, Monday, April 7, 2008 Morial Convention Center -- Hall A, Poster

Division of Chemical Education

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008