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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

Okadaic Acid Ethyl Pyruvate Diastereomeric Mixture Tiglic Acid Decanoyl Chloride 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Springer-Verlag Berlin Heidelberg 1992

Authors and Affiliations

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

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