Synthesis of the lycopodium alkaloid (+)-lycoflexine.
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.
Ramharter
Jürgen
J
Institute of Organic Chemistry, University of Vienna, Waehringer Strasse 38, 1090 Vienna, Austria. juergen.ramharter@univie.ac.at
Weinstabl
Harald
H
Mulzer
Johann
J
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D032502:Lycopodium / Q000737:chemistry*; D010084:Oxidation-Reduction
D000470:Alkaloids; C555161:lycoflexine