Total Synthesis of Highly Symmetric Squalene-Derived Cytotoxic Polyethers
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概要
- 論文の詳細を見る
In this review article, we report our recent contributions to the total synthesis of the highly symmetric squalene-derived cytotoxic triterpene polyethers, teurilene (3), (+) -14-deacetyl eurylene (1), (+) -eurylene (4), (-) -glabrescol (5), and (-) -longilene peroxide (2), based on the concept of two-directional synthesis utilizing their intrinsic molecular symmetry as the fundamental strategy. In the course of these synthetic studies, <I>syn</I> oxidative cyclizations of bishomoallylic tertiary alcohols promoted by rhenium (VII) oxide have been accomplished with excellent diastereoselectivities. The critical <I>trans</I> or <I>cis</I> selectivity between the 2- and 5-positions of the tetrahydrofuran (THF) ring in the products has been observed, depending on the substrates employed. In addition, the <I>meso</I> structure 6 originally proposed by Jacobs <I>et al</I>. has been revised to the optically pure C<SUB>2</SUB> symmetric structure 5 through its enantioselective total synthesis. Furthermore, the unknown absolute configuration of longilene peroxide has been determined by this synthesis as shown in the structural formula 2.
- 社団法人 有機合成化学協会の論文
- 2002-11-01
著者
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Morimoto Y
Osaka City Univ. Osaka
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Morimoto Yoshiki
Department Of Chemistry Graduate School Of Science Osaka City University
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KINOSHITA Takamasa
Department of Chemistry, Graduate School of Science, Osaka University
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IWAI Toshiyuki
Department of Chemistry, Graduate School of Science, Osaka City University
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Iwai Toshiyuki
Department Of Chemistry Graduate School Of Science Osaka City University
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Morimoto Y
Department Of Chemistry Graduate School Of Science Osaka City University
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Kinoshita Takamasa
Department Of Chemistry Graduate School Of Science Osaka City University
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