Studies toward the asymmetric synthesis of silvestrol

ORGN 664

Baudouin Gerard, gerard@chem.bu.edu, Department of Chemistry, Boston University, 590 Commonwealth Avenue, Boston, MA 02215 and John A. Porco Jr., porco@bu.edu, Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, 590 Commonwealth Ave., Boston, MA 02215.
The complex rocaglate silvestrol 1 was recently isolated from Aglaia silvestris. This compound was shown to exhibit very potent in vitro and in vivo cytotoxic activity comparable to the activity of the anticancer agent Taxol. In contrast to other rocaglate derivatives, silvestrol possesses a unique dioxanyloxy group at C-6 of the cyclopenta[b]benzofuran core. This presentation will outline our recent efforts toward the synthesis of 1 using enantioselective photogeneration/cycloaddition of oxidopyryliums derived from 3-hydroxyflavones

 

Total Synthesis of Complex Molecules
8:00 AM-12:00 PM, Wednesday, August 22, 2007 BCEC -- 258A, Oral

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007