ORGN 699 |
| Pyranostilbenes with the benzopyran moiety on the stilbene are found in nature. Recently, we developed a new and useful methodology for preparing a variety of benzopyrans using ethylenediamine diacetate (EDDA)-catalyzed reactions of resorcinols with a,b-unsaturated aldehydes. These reactions involve cycloadditions through an electrocyclization or hetero Diels-Alder reaction and provide a rapid route for the synthesis of benzopyran derivatives with a variety of substituents on the pyranyl ring. As part of an ongoing study of the synthetic efficacy of this methodology, we describe herein an efficient and general synthesis of a variety of pyranostilbene derivatives through a domino aldol-type reaction and an electrocyclization reaction. As an application of this methodology, we also report on the first total synthesis of the naturally occurring artocarbene and pawhuskin B. |
|
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 |