This report describes in detail the chemical structure involving the absolute configuration of a new terpenic ester.
The above compound
1 was converted to (+)-(4
S)-piperitone (
2) by treatment with alumina. Compound
1 was then reduced with LiAlH
4 to give a mixture of compound
3 (90%) and
4 (10%). The main product
3 was oxidized with the Collins' reagent to afford compound
5, which on treatment with alumina gave compound
2, while the minor product
4 corresponded to (-)-(1
S:3
R:4
S)-1-hydroxymenthol. On the other hand, compound
3 was identical with the product obtained as a result of reduction with LiAlH
4 of (+)-(1
S:2
S:3
R:4
S)-l, 2-epoxyneomenthylacetate (
7). Thus, compound
3 and
5 were assigned as (+)-(1
S:3
S:4
S)-1-hydroxyneomenthol and (-)-(1
S:4
S)-1-hydroxy-
p-menth-3-one. Compound
1 was therefore determined to be (+)-(1
S:4
S)-1-acetoxy-
p-menth-3-one. From the observed coupling constant in the NMR spectra of
3 and its acetate (
6), the conformation were also discussed.
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