10 Penitrem Dの全合成(口頭発表の部)

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The indole-diterpene tremorgens comprise a rapidly growing family of environmental toxins. The two major structural subgroups contain either unsubstituted benzene rings, as in paspaline (1), paspalicine (2), and paspalinine (3), or complex indole systems, exemplified by the lolitrems (4,5) and the penitrems (7-12). The penitrems are the most complex members of this increasingly important class of natural products. Aside from their novel architecture, our interest in the indole tremorgens stems from their biological activities. Members of this family of toxins have been implicated in a wide range of neurological disorders. Our long-standing interest in these compounds has already led to the first total syntheses of paspaline (1), paspalicine (2), and paspalinine (3). We describe herein the first total synthesis of penitrem D (10), the simplest member of the architecturally complex penitrem subfamily. The first-generation approach to penitrem D (10) featured a one-pot cyclization reaction of key intermediate 24, which was prepared from toluidine 17 and lactone 18. The key cyclization reaction of 24 proceeded to give a single product. Unfortunately, the product was found to have the undesired stereochemistry at the newly formed C28 stereocenter. We then focused on a second-generation strategy, in which coupling of aniline 37 with lactone 38 was planned for the latter stages of the synthesis. The synthesis proceeded via 17 step conversion of lactone 18 to 38. Completion of the synthetic scheme involved a 9 step transformation of 38 to penitrem D (10). The synthetic sample proved identical to the natural sample based on ^1H-NMR and TLC analyses.
1999-09-01

10 Penitrem Dの全合成(口頭発表の部)

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