Chemical Transformation of Terpenoids. I. Syntheses of (3S)-1-Vinyl-, (3S)-1-Hydroxypropenyl-, and (3S)-1-Epoxyethyl-1, 2, 2-trimethylcyclopentane Derivatives from d-Camphor via d-Camphoric Acid

抄録

As part of a series of studies on the transformation of terpenoids, four 1, 2, 2-trimethyl-cyclopentane derivatives, i.e., (+)-(1S, 3S)-3-acetoxymethyl-1, 2, 2-trimethyl-1-vinylcyclopentane (5), (+)-(1S, 3S)-3-acetoxymethyl-1-(3'-hydroxypropenyl)-1, 2, 2-trimethylcyclopentane (7), (+)-(1R, 3S, 1'S)-3-acetoxymethyl-1-(1', 2'-epoxyethyl)-1, 2, 2-trimethylcyclopentane (8), and (+)-(1R, 3S, 1'R)-3-acetoxymethyl-1-(1', 2'-epoxyethyl)-1, 2, 2-trimethylcyclopentane (9), were synthesized from d-camphor (1) via d-camphoric acid (2). All four compounds (5, 7, 8, 9) retain the C-4 configuration of d-camphor at their C-3 positions.