1: 85 percent / pyridine / 12 h 2: 91 percent / KOH / methanol / 48 h / Ambient temperature 3: 71 percent / PhCO3H / CHCl3 / 120 h / Ambient temperature 4: 1.) LiAlH4, 2.) pyridinium dichromate / 1.) Et2O, 2.) CH2Cl2, 2 h 5: 1.) NaH / 1.) Et2O, 2.) Et2O, 3 h, RT 6: POCl3, pyridine / diethyl ether / 72 h 7: 83 percent / 1 M (i-Bu)2AlH / diethyl ether; hexane / -70 - 0 °C View Scheme

acetyl chloride T=50°C; Verseifung des entstandenen Diacetats; pinol hydrate;

acetic anhydride T=150°C; Verseifung des entstandenen Diacetats mit Barytwasser;

T=200°C; inactive p-menthanetriol-(1.2.8) of melting point 121-122 degree;

T=150°C; inactive p-menthanetriol-(1.2.8) of melting point 121-122 degree;

inactive p-menthanetriol-(1.2.8) of melting point 121-122 degree;