The Journal of Organic Chemistry

Synthesis of 7-carboxytricyclo [3.3. 1.03, 7] nonan-3-ol

GE Renzoni, WT Borden

Index: Renzoni, George E.; Borden, Weston Thatcher Journal of Organic Chemistry, 1983 , vol. 48, # 26 p. 5231 - 5236

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Citation Number: 22

Abstract

The title compound (5a) has been synthesized in three steps from diol 6, which can be prepared in two steps from commercially available adamantanone. Jones oxidation of the diol gave, in addition to the desired endo keto acid (3a), diketone 11. The mechanism for formation of the diketone in this reaction is discussed in light of conformational studies carried out on the methyl ester 3b. These studies show that 3 and the C-7 epimer 4, which ...