… of prenylated quinones by the oxidative degradation approach. Birch vs vinylogous Birch hydrogenolysis (BIHY vs VIBIHY) in controlling 2. DELTA. stereochemistry of …

P Ballester, M Capo, X Garcias…

Index: Ballester, Pablo; Capo, Magdalena; Garcias, Xavier; Saa, Jose M. Journal of Organic Chemistry, 1993 , vol. 58, # 2 p. 328 - 334

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Citation Number: 12

Abstract

Two novel approaches toward prenylated quinones are described. The first (route A) involves the following three basic operations:(a) construction of a 4-hydroxybenzylamine carrying a tertiary allyl alcohol (cinnamyl alcohol) side chain of appropriate length (CS, Clot etc), follcmed by (b) vinylogous Birch reductive cleavage with concomitant isomerization of the double bond (vinylogous Birch hydrogenolysis, VIBIHY) and (c) Fremy's salt oxidative ...