テルペン類の極性非プロトン溶媒を用いる酸化反応 (第5報) : α-及びβ-セドレンの極性非プロトン溶媒中での自動酸化

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Oxygen was blown into a stirred mixture of α-cedrene (1) or β-cedrene (2) in a polar aprotic solvent (DMSO, DMF or HMPA) for 258O h at 80100°C. The oxidation of (1) in DMSO at 80°C took place to give 5-isocedranone (5), 6 (13) -cedren-5-one (6), and 5-cedren-4-one (7), while a similar oxidation of (2) yielded (5), (6), and 5-cedren-13-al (8) as major products. In DMF at 100±5°C, the oxidation of (1) gave 5α, 6α- epoxycedrane (3) that was a precursor of (5), (7), and (8), and the oxidation of (2) gave 6α, 13-epoxycedrane (4) that was a precursor of (8), (6), and 5-cedren-13-ol (9). <BR>When the oxidation of (1) was conducted in HMPA at 100±5°C, (1) was obtained selectively (68%).
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