Regiospecific functionalization of the monoterpene ether 1, 3, 3-trimethyl-2-oxabicyclo [2.2. 2] octane (1, 8-cineole). Synthesis of the useful bridged. gamma.-lactone 1, …

MV De Boggiatto, CS De Heluani…

Index: Boggiatto, Margarita V. de; Heluani, Carola S. de; Fenik, Ines J. S.; Catalan, Cesar A. N. Journal of Organic Chemistry, 1987 ,  vol. 52,  # 8  p. 1505 - 1511

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Citation Number: 29

Abstract

The regiospecific functionalization at C-5 and difunctionalization at C-5/C-8 and C-5/C-10 of the monoterpene 1, 3, 3-trimethyl-2-oxabicyclo [2.2. 2] octane (1) is described. Chromyl acetate oxidation of 1 afforded 1, 3, 3-tri-methyl-2-oxabicyclo [2.2. 2] octan-5-one (6) in 60% yield along with 28% of unreacted 1 and minor amounts of exo-1, 3, 3-trimethyl-2-oxabicyclo [2.2. 2loctan-5-01 acetate (9), 1, 3, 3-trimethyl-2-oxabicyclo [2.2. 2] octane-5, 8-dione (13), ...