The asymmetric Diels-Alder cycloaddition using ethyl (-)-(Z)-(R)s-2-methyl-3-(p-tolylsulfinyl)propenoate: Application to an enantioselective synthesis of (+)-epi-.BETA.-santalene.
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概要
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The Diels–Alder reaction of ethyl (−)-(<I>Z</I>)-(<I>R</I>)<SUB>S</SUB>-2-methyl-3-(<I>p</I>-tolylsulfinyl)propenoate (<B>6</B>) with cyclopentadiene gave the cycloadducts <B>7</B>, <B>8</B>, and <B>9</B> in a high diastereoselective manner. The cycloadduct <B>7</B> was transformed into the acetal (−)-<B>25</B>. The racemic <B>25</B> was used as an intermediate in the synthesis of (±)-β-santalol. Thus, the chiral acetal (−)-<B>25</B> should provide a route to (−)-β-santalol. The cycloadduct <B>8</B> was converted into (+)-<I>epi</I>-β-santalene in 11 steps.
- 公益社団法人 日本化学会の論文
著者
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Koizumi Toru
Faculty Of Pharmaceutical Sciences Toyama Medical & Pharmaceutical University
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ARAI Yoshitsugu
Faculty of Pharmaceutical Sciences, Gifu Pharmaceutical University
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Yamamoto Masatoshi
Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University
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