The Journal of Organic Chemistry

Convenient preparative routes to 1, 8-bishomocubane, 1, 8-bishomocubanone, snoutanone, and homocubanone

G Mehta, A Srikrishna, SC Suri

Index: Mehta, Goverdhan; Srikrishna, A.; Suri, Suresh C. Journal of Organic Chemistry, 1980 , vol. 45, # 26 p. 5375 - 5377

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Citation Number: 7

Abstract

9 3, R= H 10, R= D decarboxylation of 8 yaelded the dibromo ketal 9 which WBS dehalogenated'O with Li-THF-t-BuOH and hydrolyzed with acid to yield 3." All the steps from 8 to 3 proceeded in over 90% yield. The procedure for obtaining 3 from 8 is particularly efficacious for preparing labeled 3 required in mechanistic studies. 12 Thus, reaction of 9 with Li-THF-t-BuOD led to the formation of homocubanone-dz (10; d2= 49%, dl= 3570, do ...