Synthesis of lanopylin B1

  • J Org Chem. 2005 Feb 4;70(3):1087-8. doi: 10.1021/jo048131w.
Barry B Snider  1 ,  Jingye Zhou
Affiliations
  • 1. Department of Chemistry MS 015, Brandeis University, Waltham, MA 02454-9110, USA. [email protected]
PMID: 15675879 DOI: 10.1021/jo048131w
Abstract

Phase-transfer alkylation of diethyl 2-oxopropylphosphonate (9) with 2-iodoalkyl azide afforded 40% of azido phosphonate 6, which underwent a phase-transfer Horner-Emmons Wittig reaction with heptadecanal to provide 80% of azido enone 5. An intramolecular aza-Wittig reaction with polymer-bound Ph(3)P in toluene at reflux completed the first synthesis of lanopylin B(1) in 76% yield.

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