ORGN 661 |
(S,S)-Falcarindiol (1) is a widely distributed bioactive polyacetylene with antifungal, neurotoxic, and anti-inflammatory activities that accumulates in plants of the Apiaceae family. We have developed two synthetic paths to 1 as part of our biosynthetic studies for the diacetylene, and will contrast our methods and those reported by others. In our studies, one approach began with inexpensive isoascorbic acid, a chiral pool source, and the other employed a high-yielding asymmetric dihydroxylation chemistry to enantioselectively form propargylic alcohol 2. A dinuclear zinc-catalyzed addition to a variety of α,β-unsaturated aldehydes provided 3, allowing cross-coupling for the convergent synthesis of 1. |
Heterocycles and Aromatics, Asymmetric Reactions and Syntheses and Total Synthesis of Complex Molecules
7:00 PM-9:00 PM, Wednesday, August 19, 2009 Walter E. Washington Convention Center -- Ballroom C, Poster
Division of Organic Chemistry |