Abstract
One-carbon homologation of geranyl and farnesyl chlorides to secondary N-methylamines via α-lithioformamide alkylations followed by N-alkylation with bromoacetate esters afforded α-(homogeranylamino)- and α-(homofarnesylamino)acetates . After α-farnesylation , hydride reductions gave branched and straight-chain tertiary β-amino alcohols15 and 19. The diphosphate derivatives(7 and 8) of 15 and 19 prepared by SN 2 displacements may be regarded as aza analogs of plausible carbocation intermediaire in the biosynthesis of squalene and geranylgeranyl diphosphate since,in preliminary collaborative evaluations,they inhibit the respective synthase enzymes at micromolar concentrations
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