【新着論文】Rapid construction of a diterpene-inspired tetracyclic skeleton bearing bicyclo[3.2.1]octane rings based on desymmetrization of 1,3-diketones

ビシクロ[3.2.1]オクタン環を有する天然物類似多環性骨格の迅速合成に関する鎌田くんの論文がアクセプトされました！

Hidetoshi Kamada, Haruki Mizoguchi*, Akira Sakakura*
Tetrahedron Letters 2024, 157, 155470

A synthetic methodology for constructing ent-kaurane-like tetracyclic skeletons possessing a bicyclo[3.2.1]octane moiety has been developed by employing a desymmetrizing sequential cyclization strategy. Using a symmetric diketone as a key branching point, the sequence of desymmetric Friedel–Crafts cyclization and Pd-catalyzed intramolecular α-vinylation of ketone allowed us to construct the ent-kaurane-like tetracyclic skeleton from 1,3-cyclohexanedione in four steps. In contrast, reversing the order of the cyclization steps yielded a pseudo-symmetric tetracyclic skeleton, which is also reminiscent of the kaurane framework.

https://www.sciencedirect.com/science/article/pii/S004040392500019X