The Synthesis of 2,3-Dimethyl-3-(5-bromo-2-methoxy-4-methylphenyl)-cyclohexene, a Potentially Useful Intermediate for the Syntheses of Aplysin and Related Sesquiterpenes
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概要
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As a key intermediate for the syntheses of aplysin, <B>1</B>, a bromine-containing sesquiterpene isolated from <I>Aplysia kurodai</I>, and related sesquiterpenes, 2,3-dimethyl-3-(5′-bromo-2′-methoxy-4′-methylphenyl)cyclohexene, <B>2</B>, was synthesized, starting from an anisole derivative, <B>6</B>. The reactivity of the double bond in <B>2</B> towards oxidizing reagents was examined: the cyclohexene, <B>2</B>, reacted with ozone to give an epoxide, <B>12</B>, and a cyclohexanone, <B>13</B>; an isomerization product of <B>12; 2</B> could be converted to the diol, <B>15</B>, with osmium tetroxide in the presence of pyridine.
- 公益社団法人 日本化学会の論文
著者
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Yamada Kiyoyuki
Department Of Chemistry Faculty Of Science Nagoya University
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Hirata Yoshimasa
Department of Chemistry, Faculty of Science, Nagoya University
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Yazawa Hisatoyo
Department of Chemistry, Faculty of Science, Nagoya University
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