ORGN 666 |
| Through significant advances in organic methodology, total synthesis remains one of the most significant ways to bring anti-cancer agents from the outside into our medicine cabinets. Pyrancin, a structurally-unique member of the annonaceous acetogenin family of natural products, demonstrates selective cytotoxicity against both human pancreatic and promyelocytic cells, and its unique mode of action makes it an attractive candidate as a multi-drug resistant cancer therapy. Its total synthesis has been reported. The butenolide ring was constructed via an asymmetric alkylation/ring-closing metathesis strategy. The four stereocenters of the left-hand tetrahydropyran ring were installed by efficient chiral auxiliary-mediated aldol reactions. Convergent closure of the tetrahydropyran and fusion of the alkyl backbone were affected via sequential ring-closing metathesis/dimerization/cross metathesis reactions.
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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 |
