Scripps VIVO scripps research logo

  • Index
  • Log in
  • Home
  • People
  • Organizations
  • Research
  • Events
Search form

Total syntheses of anominine and tubingensin a

Academic Article
uri icon
  • Overview
  • Identity
  • Additional Document Info
  • View All
scroll to property group menus

Overview

authors

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

publication date

  • May 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
scroll to property group menus

Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja302765m

PubMed ID

  • 22537293
scroll to property group menus

Additional Document Info

start page

  • 8078

end page

  • 8081

volume

  • 134

issue

  • 19

©2021 The Scripps Research Institute | Terms of Use | Powered by VIVO

  • About
  • Contact Us
  • Support