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One of us has reported1 that hibalactone (I), C20H16O6, m.p. 146-146.5°, [ ]23 -87°( chloroform), isolated from young leaves of chyabohiba, nikohiba or Chamaecyparis obtusa (Cupressiacenae),2 has the structure shown in Cmpd. I. This structure was established by the production of piperonylic acid, piperonal and oxalic acid either by permanganate oxidation or ozonolysis, by hydrogenation (Raney nickel or sodium amalgam) to ( + )-isohinokinin3 (major product) and ( -)-hinokinin3 (minor product) by spectroscopic evidence pointing to an ,/3-unsaturated lactone structure, and by studies of the hydrolysis, nitration and bromination products of I.

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