Synthetic elaboration of diosphenols. Part 3. Replacement of enolic oxygen by hydrogen

…, O Zaim, Y Pazo, L Ohannesian

Index: Ponaras, Anthony A.; Zaim, Oemer; Pazo, Yessica; Ohannesian, Lena Journal of Organic Chemistry, 1988 , vol. 53, # 5 p. 1110 - 1112

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Citation Number: 14

Abstract

In the course of applying the diosphenol Claisen rearrangement'to natural products synthesis, we desired to deoxygenate C-allylated diosphenols in the sense ac (Figure 1). Reported sequences2 for effecting this transformation involve a catalytic hydrogenation step incompatible with preservation of the allyl group. In our hands lithium/ammonia reduction of diosphenol methyl ethers gave predominantly a-methoxy ketones; similar reduction of ...