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Polycyclic framework synthesis of anominine and tubingensin A indole diterpenoids. | LitMetric
A highly congested decalin embodying an alpha-methylene ketone is synthesized in 11 steps from the Wieland-Miescher ketone and efficiently converted to the polycyclic frameworks of anominine and tubingensin A, which constitutes the first approach to the skeleton of these indole diterpenoids.
Similar Publications
Shanghai Institute of Organic Chemistry , Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
A divergent strategy for the total syntheses of the indole terpenoid anominine (1) and its natural congener tubingensin A (2) has been developed. The common intermediate 11 bearing all of the required stereogenic centers for both natural products was first assembled by employing a Ueno-Stork radical cyclization and a Sc(OTf)(3)-mediated Mukaiyama aldol reaction to form the key C-C bonds in a stereocontrolled manner. The route to anominine features a radical deoxygenation followed by an efficient side-chain installation, while the path to tubingensin A exploits a CuOTf-promoted 6π-electrocyclization/aromatization sequence to forge the central region of the pentacyclic scaffold.
Universitat de Barcelona , Av. Joan XXIII s/n, 08028-Barcelona, Spain.
A highly congested decalin embodying an alpha-methylene ketone is synthesized in 11 steps from the Wieland-Miescher ketone and efficiently converted to the polycyclic frameworks of anominine and tubingensin A, which constitutes the first approach to the skeleton of these indole diterpenoids.
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