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Chemistry. 2013 Jun 24;19(26):8665-72. doi: 10.1002/chem.201300364. Epub 2013 May 6.

Total syntheses of (±)-fawcettimine, (±)-fawcettidine, (±)-lycoflexine, and (±)-lycoposerramine-Q.

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  • 1Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.


The total syntheses of four fawcettimine-related Lycopodium alkaloids, (±)-fawcettimine, (±)-fawcettidine, (±)-lycoposerramine-Q, and (±)-lycoflexine, were completed in a highly stereoselective manner. The Pauson-Khand reaction of 4-methylidene-6-siloxyoct-1-en-7-yne followed by regio- and stereoselective hydrogenation led to the short-step preparation of the bicyclo[4.3.0]nonenone intermediate bearing a methyl group with the required stereochemistry. The subsequent chemical manipulation of the bicyclic compound afforded the 6-5-9-membered tricyclic dioxo compound, which was then transformed into the four targeted alkaloids in an alternative and more efficient fashion.

Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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