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Chemistry of Natural alpha-Amino Acids: A Surprising "One-Pot Four-Step" Conversion of Polyfunctional Enones into Cyclic Imines

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Sonia Amigoni , Christophe Penverne , Caroline Nugier-Chauvin and Yves Le Floc'h

Ecole Nationale Supérieure de Chimie, Campus de Beaulieu, 35700 Rennes, France

J. Chem. Educ., 1999, 76 (9), p 1247

DOI: 10.1021/ed076p1247

Publication Date (Web): September 1, 1999

Section:

History, Education, and Documentation

Abstract

This project is aimed at introducing graduate students to multistep organic synthesis. The elaboration of the proposed retrosynthetic scheme involved the use of natural a-amino acids as starting materials. The synthesis of the target polyfunctional enones allowed students to understand the importance of protective groups. They also discovered the necessity of intermediate purification even at the price of lower yields. The use of sensitive and harmful reagents such as DIBALH, for instance, led the instructors to point out laboratory work hazards and to remind students of elementary safety instructions. Hydrogenation and hydrogenolysis of these enones afforded original analogues of natural alkaloids, the structure of which was elucidated by NMR spectroscopy and IR spectrometry.

Keywords (Audience):

Graduate Education / Research

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Natural Products

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This article has been cited by 1 ACS Journal articles (1 most recent appear below).

Synthesis and Analysis of a Versatile Imine for the Undergraduate Organic Chemistry Laboratory
Jacqueline Bennett , Kristen Meldi and Christopher Kimmell II
Journal of Chemical Education2006 83 (8), 1221
- Synthesis and Analysis of a Versatile Imine for the Undergraduate Organic Chemistry Laboratory
  Jacqueline Bennett , Kristen Meldi and Christopher Kimmell II
  Journal of Chemical Education2006 83 (8), 1221
  An important synthesis omitted from organic laboratory texts is that of imine preparation, a particularly relevant intermediate both synthetically and biologically. In this experiment students prepare and analyze N-p-methoxyphenyl (N-PMP) α-imino ethyl ...
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