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31st May 2013
Synthesis of a Highly Functionalized Core of Verrillin, A. Saitman, E. A. Theodorakis, Org. Lett., 2013, 15, 2410.
Gorgonian octocorals and soft corals supply a diverse array of diterpenes and C4-norditerpenes that biosynthetically derive from a 14-membered cembrane skeleton. Among them, verrillin is highlighted by a combination of intricate structural density and potent bioactivity. This paper provided a stereoselective synthesis of furanoverrillin, a branching node toward the synthesis of verrillin and related polycyclic cembrenoids. Their approach relies on introduction of the C7-C11 cyclopentene ring prior to the macrocyclization of the fully functionalized verrillin core.They observed that the presence of a C4 methyl group at the furan ring increases its susceptibility toward oxidative decomposition. In turn, this attests to the role of the C4 methyl group in oxidative rearrangements that account for the plethora of polycyclic cembranes isolated thus far.