Total synthesis of naphthylisoquinoline alkaloids

https://doi.org/10.1016/S1572-5995(97)80035-XGet rights and content

Publisher Summary

This chapter describes the plant families, Ancistrocladaceae and Dioncophyllaceae, which are the only identified sources of the unusual naphthylisoquinoline alkaloids. The family, Ancistrocladaceae contains one genus, Ancistrocladus, which consists of approximately 20 species that are distributed in the Indian archipelago, tropical Asia, and tropical West Africa. Naphthylisoquinoline alkaloids are structurally unusual on the account of the methyl group present at the 3-position and oxygenation at the 8- and/or 6-position of the isoquinoline ring, which points to a polyketide origin. It has been proposed that both the naphthalene and isoquinohne moieties of these compounds could arise from a common polyketide precursor. For the biomimetic synthesis of 1,3-dimethyltetrahydroisoquinolines, Bringmann studied the condensation of diketones with pyridoxamine phosphate equivalents. It was found, however, that the desired reductive amination did not occur. Because the naphthylisoquinoline alkaloids occur as stable atropisomers, a key aspect of their synthesis is the stereocontrolled construction of the biaryl linkage. A number of methods have been developed for the synthesis of unsymmetrical chiral biaryls and can be divided into inter- and /intramolecular approaches.

References (96)

  • G. Bringmann et al.

    Tetrahedron Lett.

    (1984)
  • G. Bringmann

    The Alkaloids

  • S. Heinzman et al.

    Tetrahedron Lett.

    (1980)
  • G. Bringmann et al.

    Phytochemistry

    (1992)
  • J.-P. Foucher et al.

    Phytochemistry

    (1974)
  • G. Bringmann et al.

    Tetrahedron Lett.

    (1990)
  • G. Bringmann et al.

    Tetrahedron

    (1994)
  • T.R. Kelly et al.

    Tetrahedron Lett.

    (1994)
  • T.R. Hoye et al.

    Tetrahedron Lett.

    (1994)
  • T.R. Hoye et al.

    Tetrahedron Lett.

    (1996)
  • T.R. Hoye et al.

    Tetrahedron Lett.

    (1996)
  • Z.X. Chen et al.

    Yaoxue Xuebao

    (1981)
  • T.R. Govindachari et al.

    Indian J. Chem.

    (1972)
  • T.R. Govindachari et al.

    J. Chem. Soc., Perkin Trans. 1

    (1975)
  • T.R. Govindachari et al.

    Indian J. Chem.

    (1973)
  • K.P. Manfredi et al.

    J. Med. Chem.

    (1991)
  • G. Bringmann et al.

    Angew. Chem. Int. Ed. Engl.

    (1993)
  • M.R. Boyd et al.

    J. Med. Chem.

    (1994)
  • J. Bruncton et al.

    Phytochemistry

    (1976)
  • G. Bringmann

    Angew. Chem. Int. Ed. Engl.

    (1982)
  • G. Bringmann et al.

    Heterocycles

    (1986)
  • G. Bringmann et al.

    Angew. Chem., Int. Ed. Engl.

    (1990)
  • A.I. Meyers et al.

    Tetrahedron

    (1994)
  • A.I. Meyers et al.

    J. Am. Chem. Soc.

    (1982)
  • A.I. Meyers et al.

    J. Am. Chem. Soc.

    (1985)
  • A.I. Meyers et al.

    Tetrahedron Lett.

    (1993)
  • M.A. Rizzacasa et al.

    J. Chem. Soc., Perkin Trans. 1

    (1991)
  • J.M. Wilson et al.

    J. Am. Chem. Soc.

    (1982)
  • T. Hattori et al.

    J. Chem. Soc., Perkin Trans. 1

    (1994)
  • M. Uemura et al.

    J. Org. Chem.

    (1996)
  • A.I. Meyers et al.

    J. Am. Chem. Soc.

    (1990)
  • K. Kamikawa et al.

    Synlett

    (1995)
  • M. Shindo et al.

    J. Am. Chem. Soc.

    (1992)
  • T. Hayashi et al.

    J. Am. Chem. Soc.

    (1988)
  • M. Tanaka et al.

    Tetrahedron Lett.

    (1992)
  • D.A. Evans et al.

    J. Am. Chem. Soc.

    (1993)
  • G. Bringmann et al.

    Heterocycles

    (1989)
  • G. Bringmann et al.

    Liebigs Ann. Chem.

    (1992)
  • Cited by (0)

    View full text