Stereo- and regiocontrolled hydroxylation of oxyallyl [4+3] cycloadducts. A concise synthesis of hinokitiol

Article abstract of DOI:10.1016/S0040-4039(99)01589-0

Stereo- and regioselective hydroxylation of 8-oxabicyclo[3.2.1]oct-6-en-3-ones was achieved by the action of (diacetoxyiodo)benzene in methanolic potassium hydroxide (the Moriarty oxidation). Subsequent double elimination afforded a convenient preparation of substituted tropolones, as exemplified in a three-step synthesis of hinokitiol (1).