ORGN 431 | |||
| Aerial parts of T. chamaedrys have been investigated for their chemical constituents. These include saponins, glycosides, flavonoids and a number of furan-containing clerodane diterpenoids, the most abundant of which is teucrin A (1). The structure and stereochemistry of teucrin A have been described by Popa et al. in 1973. We have recently embarked on a project directed towards the total synthesis of furan-containing nor-clerodane diterpenoids. Under zinc chloride catalysis, the Diels-Alder addition of 2,4-pentadienol to enone 2, readily prepared from diethyl succinate in five steps, proceeded with complete face-, regio-, and stereoselectivity to give adduct 3. This compound was converted to the advanced intermediate 4 via a sequence of eight synthetic operations. The transformation of this projected synthetic intermediate to the target natural products is under current investigation. Details of the synthetic studies will be described. .
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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 |
