Synthesis of the 1-phenethyltetrahydroisoquinoline alkaloids (+)-dysoxyline, (+)-colchiethanamine, and (+)-colchiethine

J Org Chem. 2012 Dec 21;77(24):11101-8. doi: 10.1021/jo302157e. Epub 2012 Dec 6.

Abstract

Asymmetric total syntheses of the 1-phenethyl-1,2,3,4-tetrahydroisoquinoline alkaloids (+)-dysoxyline (1), (+)-colchiethanamine (2), and (+)-colchiethine (3) are described. In the synthetic routes, coupling of a key, enatiomerically pure 1-(sulfonylmethyl)tetrahydroisoquinoline with aromatic aldehydes, performed by using the Julia-Kocienski reaction, afforded the corresponding 1-(β-styryl)-substituted tetrahydroisoquinolines with complete retention of the absolute configuration at the C1 carbon atom. Functionalization of the products generated in these processes by using four- or five-step sequences gave the target alkaloids 1-3.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry*
  • Alkenes / chemistry
  • Chemistry Techniques, Synthetic
  • Isoquinolines / chemical synthesis*
  • Isoquinolines / chemistry*

Substances

  • Alkaloids
  • Alkenes
  • Isoquinolines
  • colchiethanamine
  • colchiethine
  • dysoxyline
  • isoquinoline