Synthesis of lanopylin B1.
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.
Snider
Barry B
BB
Department of Chemistry MS 015, Brandeis University, Waltham, MA 02454-9110, USA. snider@brandeis.edu
Zhou
Jingye
J
D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D019751:Intramolecular Transferases / Q000037:antagonists & inhibitors
D000473:Alkanes; D001372:Aza Compounds; D004791:Enzyme Inhibitors; C500685:lanopylin B1; D019751:Intramolecular Transferases; C021924:lanosterol synthase