A convenient synthesis of immunosuppressive agent FTY720 using the petasis reaction

Chem Pharm Bull (Tokyo). 2005 Jan;53(1):100-2. doi: 10.1248/cpb.53.100.

Abstract

A convenient synthesis of immunosuppressive agent FTY720 (1) using the Petasis reaction was developed. 4-Octylbenzaldehyde (9) was converted into 1-ethenyl-4-octylbenzene (11) by two-step synthesis. Hydroboration of 11 using catecholborane and hydrolysis gave (E)-2-(4-octylphenyl)vinylboronic acid (4). The Petasis reaction of 4, dihydroxyacetone (3), and benzylamine following catalytic hydrogenation afforded FTY720 (1).

MeSH terms

  • Benzylamines / chemistry
  • Benzylamines / metabolism
  • Catalysis
  • Dihydroxyacetone / chemistry
  • Dihydroxyacetone / metabolism
  • Fingolimod Hydrochloride
  • Hydrogenation
  • Immunosuppressive Agents / chemical synthesis*
  • Immunosuppressive Agents / metabolism
  • Propylene Glycols / chemical synthesis*
  • Propylene Glycols / metabolism
  • Sphingosine / analogs & derivatives

Substances

  • Benzylamines
  • Immunosuppressive Agents
  • Propylene Glycols
  • benzylamine
  • Fingolimod Hydrochloride
  • Sphingosine
  • Dihydroxyacetone