Total Synthesis and Stereochemical Revision of the Chlorinated
Sesquiterpene (+)-Gomerone C**
Nikolas Huwyler and Erick M. Carreira*
Red algae from the genus Laurencia (Ceramiales) are the
source of over 500 halogenated terpenes, cyclic ethers, and
acetogenides, which in some cases have been suggested to
serve as chemical defence agents because of their activity
against pathogenic marine bacteria and herbivores.In 2008
a Spanish research group reported the isolation and structural
elucidation of three novel chlorinated sesquiterpenes, gomerones A-C, from samples of Laurencia majuscula collected at
the southern coast of La Gomera, Canary Islands.
The structurally interesting and unprecedented
gomerane skeleton in combination with their unexplored
biological activity as well as the halogenated nature of these
natural products rendered them noteworthy targets for
synthesis.