Identification and Synthesis of Luteolide, a Highly Branched Macrolide Semiochemical from the Mantellid Frog Gephyromantis luteus

Org Lett. 2019 Apr 19;21(8):2851-2854. doi: 10.1021/acs.orglett.9b00852. Epub 2019 Apr 4.

Abstract

Luteolide is a 10-membered aliphatic macrolactone, (4 R,8 S,9 S)-4,8-dimethylundecan-9-olide ((-) -17), released by the femoral gland of males of the mantellid frog Gephyromantis luteus. Its structure was established using NMR, MS, and chiral GC and confirmed by stereoselective synthesis of different stereoisomers. Among the approximately 20 current macrolides known from the Mantellidae, luteolide is the first example of a volatile macrolide furnishing three stereogenic centers and an ethyl side chain.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anura
  • Catalysis
  • Macrolides / chemical synthesis*
  • Macrolides / isolation & purification*
  • Male
  • Molecular Structure
  • Oxidation-Reduction
  • Pheromones / chemical synthesis*
  • Pheromones / isolation & purification*
  • Stereoisomerism
  • Volatile Organic Compounds / chemical synthesis*
  • Volatile Organic Compounds / isolation & purification*

Substances

  • Macrolides
  • Pheromones
  • Volatile Organic Compounds