Quinolizidines. XXXII. A chiral synthesis of 3,4,5,6-tetradehydro-17-hydroxycorynanium, the zwitterionic structure assigned to an alkaloid from Aspidosperma marcgravianum

  • Fujii T
  • Ohba M
  • Ohashi T
  • 4

    Readers

    Mendeley users who have this article in their library.
  • 16

    Citations

    Citations of this article.

Abstract

The total synthesis of 3,4,5,6-tetradehydro-17-hydroxycorynanium [(+)-4], the zwitterionic structure assigned to an alkaloid from Aspidosperma marcgravianum, has been accomplished for the first time via a "lactim ether route". The route started with an initial condensation between the lactim ether [(+)]-5] and 3-chloroacetylindole and proceeded through the lactam ester [(+)-23], lactam alcohol [(+)-24], acetoxylactam [(+)-26], quaternary iminium salt [(+)-25], and 3,4,5,6-tetradehydro-17-hydroxycorynanium perchlorate [(+)-27]. The1H NMR spectral data and the sign of specific rotation for the synthetic (+)-4 were in disagreement with those reported for a natural sample, leaving the chemistry of this A. marcgravianum alkaloid incomplete. © 1993.

Get free article suggestions today

Mendeley saves you time finding and organizing research

Sign up here
Already have an account ?Sign in

Find this document

Authors

  • Tozo Fujii

  • Masashi Ohba

  • Takako Ohashi

Cite this document

Choose a citation style from the tabs below

Save time finding and organizing research with Mendeley

Sign up for free