Synfacts 2014; 10(11): 1117
DOI: 10.1055/s-0034-1379259
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Syntheses of (+)-Flabellidine and (–)-Lycodine

Erick M. Carreira
Mathias J. Jacobsen
Azuma M, Yoshikawa T, Kogure N, Kitajima M, Takayama H * Chiba University, Japan
Biogenetically Inspired Total Syntheses of Lycopodium Alkaloids, (+)-Flabellidine and (–)-Lycodine.

J. Am. Chem. Soc. 2014;
136: 11618-11621
Further Information

Publication History

Publication Date:
20 October 2014 (online)



In the wake of their interesting biological activities, Lycopodium alkaloids have attracted great attention from the synthetic community. A biosynthetic pathway has been proposed, in which the skeleton is constructed via a cyclization cascade. Inspired by this hypothesis, Takayama and co-workers report a successful implementation of this strategy leading to a synthesis of (–)-lycodine and the first synthesis of (+)-flabellidine.



Subjecting B to (+)-CSA triggered a cascade resulting in the formation of four rings and three contiguous stereogenic centers. Upon one-pot debenzylation–N-Boc protection of the C and D mixture, the obtained diastereomers E and F were separated, with E being further elaborated to the target natural products (+)-flabillidine and (–)-lycodine.