[CH2:1]1[CH2:15][CH2:14][CH2:13][CH:12]=[CH:11][CH:10]2[CH:6]([CH2:7][O:8][CH2:9]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])(=[O:18])C.[Na+].C(OO)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH:10]12[CH2:9][O:8][CH2:7][CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][CH2:15][CH2:14][CH2:13][CH:12]1[CH:11]2[O:18]1Muscogene (478 g, 2.4 mol), sodium acetate (63 g, 0.76 mol) and ethyl acetate (500 mL) were charged into a flask. The reaction was cooled to 0° C. While the temperature was maintained at 0° C., peracetic acid (32%, 500 mL, 2.38 mol) was dropped in over an hour and the reaction mixture was stirred for another 2 hours. Saturated sodium carbonate solution (100 mL) and toluene (50 mL) were added. The organic layer was separated and washed with brine (200 mL). The crude was purified to provide 3,15-dioxa-tricyclo[11.3.0.0*2,4*]hexadecane (462 g, ˜85% yield).
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