ORGN 427 |
| Schweinfurthin G (1) was identified in an extract of the fruit of Macaranga alnifolia by Kingston and coworkers. The total synthesis of this natural product has been accomplished through a sequence based on a cascade cyclization of the epoxide 2. Use of a synthetic strategy that relies upon a Shi epoxidation to introduce the initial stereogenic center allows this key intermediate to be prepared either through a regioselective epoxidation of a geranylated arene, or via epoxidation of a geranyl ester and subsequent attachment of the isoprenoid to an aromatic system. The relative advantages of these approaches, as well as details of the total synthesis of this natural product, will be presented.
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New Reactions and Methodology, Total Synthesis, Materials, Devices and Switches, Lipids, Nucleotides and Mimetics
8:00 PM-10:00 PM, Tuesday, March 27, 2007 Hyatt Regency Chicago -- Riverside Center, Poster
Division of Organic Chemistry |
