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Naturstoffsynthese In der Zuschrift auf S. 23290 präsentieren Chihiro Tsukano, Yoshiji Takemoto et al. die asymmetrische Totalsynthese von Shagen A und B.
We report the first total synthesis of shagenes A and B, which are tricyclic terpenoids containing a cis‐substituted cyclopropane, via ring‐closing metathesis of an enamide and Ir‐catalyzed double‐bond isomerization of an alkylidenecyclopropane. Chemo‐ and diastereoselectivity in the distorted cis‐substituted structures were controlled by the alkylidenecyclopropane reactivity and using the ketone...
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