Synthesis of Lanopylin B₁

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.