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J. Am. Chem. Soc. In Journal of the American Chemical Society, Vol. 134, No. 19. (26 April 2012), pp. 8078-8081, doi:10.1021/ja302765m Key: citeulike:12080746
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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.
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