Miscellaneous Metabolites

  • K. F. Albizati
  • V. A. Martin
  • M. R. Agharahimi
  • D. A. Stolze
Part of the Bioorganic Marine Chemistry book series (BMC, volume 6)

Abstract

Delesserine (2226) is a secondary metabolite isolated from the alga Delesseria sanguinea (Lamouroux). Its relative configuration has been determined by X-ray crystal structure analysis [600]. Although aqueous extracts of D. sanguinea collected on the European Atlantic coast are powerful anticoagulants for human blood [601], delesserine does not exhibit this property. The first synthesis of 2226, by Seebach [602], is shown in Scheme 395. Condensation of ester 2222 with aldehyde 2223 (available in four steps from diethyl tartrate) gives a mixture of four diastereomers 2224. Oxidation of 2224 and treatment with TsOH in methanol provides lactone 2225 in 32% yield along with 59% of its diastereomer. Removal of the benzyl protecting groups affords (+)-delesserine in four steps (eight steps from diethyl tartrate) and 18% overall yield.

Keywords

Aldehyde Diol Enolate Ephedrine Aldol 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Copyright information

© Springer-Verlag Berlin Heidelberg 1992

Authors and Affiliations

  • K. F. Albizati
  • V. A. Martin
  • M. R. Agharahimi
  • D. A. Stolze

There are no affiliations available

Personalised recommendations