Monatshefte für Chemie / Chemical Monthly

, Volume 128, Issue 10, pp 995–1008 | Cite as

Synthese des (±)-Rosmarinsäuremethylesters

  • E. Reimann
  • H. -J. Maas
  • T. Pflug
Organische Chemie Und Biochemie

Synthesis of (±)-rosmarinic acid methylester

Summary

Regioselective cleavage of the glycidic ester3 by BF3/ether to pyruvic acid ester4 followed by NaBH4 reduction affords the lactic acid derivative5a which in turn can be acylated by caffeoyl chloride8c to yield the O-protected rosmarinic acid ester9a. Alternatively,9a can be prepared by acylation of5a with diethylphosphono acetyl chloride (6c) thus generating theWadsworth-Emmons reagent7a which is subsequently reacted with the aldehyde1a. The analogous reaction using the silyl protected educts7d and1b failed to give9d. Finally,9a is debenzylated by BCl3 furnishing the title compound10a in fair total yield.

Keywords

Cleavage of benzyl ether and glycidic ester Phosphonate-olefin formation Diethylphosphono acetylchloride 3-(3,4-Dibenzyloxy)-phenyl lactic acid methylester O-Dibenzyl-caffeic acid (±)-Rosmarinic acid methylester 

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Copyright information

© Springer-Verlag 1997

Authors and Affiliations

  • E. Reimann
    • 1
  • H. -J. Maas
    • 1
  • T. Pflug
    • 1
  1. 1.Institut für Pharmazie und Lebensmittelchemie der Ludwig-Maximilians-Universität MünchenMünchenBundesrepublik Deutschland

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