Studies on Synthesis and Stereochemistry of 3-Methyloctahydroisocoumarins and 1-Methyloctahydro-3H-2-benzopyran-3-ones
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Four stereoisomers of 3-methyloctahydroisocoumarins (4a-d)and two 1-methyloctahydro-3H-2-benzopyran-3-ones (10a, b) were synthesized. The stereochemical correlations including the configurations of the ring juncture and the methyl group and also the ring conformations of these six lactones were investigated by chemical means and by nuclear magnetic resonance (NMR) spectrometry, such as two-dimensional(2D) NMR and steady-state ^1H-^1H nuclear Overhauser effect experiments. It was concluded that the lactone ring of 4b, c, and 10a adopts a boat or a slightly distorted boat conformation in solution.
- 公益社団法人日本薬学会の論文
- 1989-06-25
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