Total syntheses of anominine and tubingensin a

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Overview

authors

• Bian, M.
• Wang, Z.
• Xiong, X. C.
• Sun, Y.
• Matera, C.
• Nicolaou, K.C.
• Li, Ang

publication date

• 2012

journal

• Journal of the American Chemical Society  Journal

abstract

• 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.

subject areas

• Alkenes
• Biological Products
• Carbazoles
• Chemistry Techniques, Synthetic
• Indoles
• Models, Molecular
• Molecular Conformation

Identity

International Standard Serial Number (ISSN)

• 0002-7863

Digital Object Identifier (DOI)

• 10.1021/ja302765m

PubMed ID

• 22537293

Additional Document Info

start page

• 8078

end page

• 8081

volume

• 134

issue

• 19