Alkaloids from marine organisms, Part 5. Biomimetic total synthesis of lamellarin L by coupling of two different arylpyruvic acid units

Chemistry. 2000 Apr 3;6(7):1147-52. doi: 10.1002/(sici)1521-3765(20000403)6:7<1147::aid-chem1147>3.3.co;2-t.

Abstract

Reaction of the ethyl 3-arylpyruvate 5a with the methyl 2-bromo-3-arylpyruvate 6b in the presence of the 2-arylethylamine 4 afforded the pyrrole derivative 10, which could be transformed into lamellarin L (1) in five steps. The synthesis proceeds with 38% overall yield and mimics the probable biosynthesis of these marine alkaloids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis
  • Alkaloids / chemistry
  • Animals
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Benzopyrans / chemical synthesis
  • Benzopyrans / chemistry*
  • Coumarins*
  • Heterocyclic Compounds, 4 or More Rings*
  • Isoquinolines / chemical synthesis
  • Isoquinolines / chemistry*
  • Mollusca / chemistry
  • Pyrroles / chemistry
  • Pyruvates / chemistry*

Substances

  • Alkaloids
  • Antineoplastic Agents
  • Benzopyrans
  • Coumarins
  • Heterocyclic Compounds, 4 or More Rings
  • Isoquinolines
  • Pyrroles
  • Pyruvates
  • lamellarin L