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J Am Chem Soc. 2010 Oct 20;132(41):14338-9. doi: 10.1021/ja107533m.

Synthesis of the lycopodium alkaloid (+)-lycoflexine.

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  • 1Institute of Organic Chemistry, University of Vienna, Waehringer Strasse 38, 1090 Vienna, Austria. juergen.ramharter@univie.ac.at


The first total synthesis of (+)-lycoflexine (1), a constituent of Lycopodium clavatum var. inflexum , has been accomplished in eight steps with 13% overall yield. Our synthesis covers four one-pot reactions, including a tandem Sakurai/aldol sequence, a novel hydroboration/oxidation procedure, a deprotection/transannular Mannich reaction, and as a highlight, a tandem catalysis cascade combining an enynene ring-closing metathesis and a selective hydrogenation.

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