Total Syntheses of Herqulines B and C

Corinna Schindler presents the total syntheses of two herqulines.

The herqulines were initially isolated from Penicillium herquei in 1979 by Omura and co-workers. Preliminary biological evaluations of these compounds revealed that the herquline congeners are effective inhibitors of platelet aggregation and influenza virus replication. Architecturally, these small, highly strained alkaloids bear an unsymmetrical N-methyl Lewis basic piperazine core residing at the base of a bowl-shaped macrocycle. Additionally, two bridging β,γ-cyclic enones constitute the northern portion of 2 and 3. The group of Professor Corinna Schindler at the University of Michigan (USA) became interested in these structures as targets due to the challenge in synthesizing the highly strained core.

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