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. Author manuscript; available in PMC: 2008 Sep 11.
Published in final edited form as: J Am Chem Soc. 2005 Dec 21;127(50):17921–17937. doi: 10.1021/ja055967n

Scheme 12.

Scheme 12

Model studies for dioxenone formation.a

a Reagents and conditions: (a) 3 equiv. isopropenyl acetate, 3 equiv. LDA, −78 °C, 5 min. (b) 4 equiv. PCC, 1 equiv. NaOAC, 4 Å MS, CH2Cl2, 18 h, 24% (2 steps). (c) toluene-acetone (100 equiv.) 2:1 v/v, 90 °C, 40 min, 77%.