Chemical Transformation of Terpenoids. III. Syntheses of (3R)-1-Vinyl-, (3R)-1-Hydroxypropenyl-, and (3R)-1-Epoxyethyl-5-methoxy-1, 2, 2-trimethylcyclopentane Derivatives from d-Camphor via 5-Oxo-d-bornyl Acetate

抄録

As a continuation of our transformation studies on terpenoids, three optically active 5-methoxy-1, 2, 2-trimethylcyclopentane derivatives, i.e., (+)-(1R, 3R, 5S)-3-acetoxymethyl-5-methoxy-1, 2, 2-trimethyl-1-vinylcyclopentane (7), (+)-(1R, 3R, 5S)-3-acetoxymethyl-1-(3'-hydroxypropenyl)-5-methoxy-1, 2, 2-trimethylcyclopentane (8), and (-)-(1R, 3R, 5S, 1'R)-3-acetoxymethyl-1-(1', 2'-epoxyethyl)-5-methoxy-1, 2, 2-trimethylcyclopentane (9), were synthesized from d-camphor (1) via 5-oxo-d-bornyl acetate (6). All three compounds (7, 8, 9) retain the C-4 configuration of d-camphor at their C-3 positions.