Total syntheses of (+)-altholactone[(+)-goniothalenol] and three stereocongeners and their cytotoxicity against several tumor cell lines.
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概要
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Enantiospecific total synthesis of (+)-altholactone [(+)-goniothalenol] (<B>1</B>), a novel tetrahydrofuropyran-5-one possessing significant cytotoxicity against several tumor cell lines, has been achieved by using L-arabinose as the redundant starting material. The pivotal tetrahydrofuran formation was realized by treatment of the diastereomeric mixture of (2<I>S</I>,3<I>R</I>)-4,5-epoxy-5-phenyl-1,2,3-pentanetriol 1,3-benzylidene acetals <B>8</B> and <B>8</B>′ with silica gel. Simultaneous stereochemical inversion at C-4 and C-5 of the major cyclization product, <I>O</I>,<I>O</I>′-benzylidene derivative of (2<I>S</I>,3<I>R</I>,4<I>S</I>,5<I>S</I>)-2-(hydroxymethyl)-5-phenyltetrahydrofuran-3,4-diol (<B>11</B>), to the 2<I>S</I>,3<I>R</I>,4<I>R</I>,5<I>R</I> diastereomer <B>10</B> was achieved by hydroboration of (2<I>S</I>,3<I>S</I>)-3-hydroxy-2-(hydroxymethyl)-5-phenyl-2,3-dihydrofuran <I>O</I>,<I>O</I>′-benzylidene derivative (<B>18</B>) which derived from <B>11</B>. Pfitzner-Moffatt oxidation of <B>10</B> followed by NaBH<SUB>4</SUB> reduction gave the 2<I>S</I>,3<I>R</I>,4<I>S</I>,5<I>R</I> diastereomer <B>20</B> exclusively. Displacement of the triflate group in (2<I>S</I>,3<I>R</I>,4<I>S</I>,5<I>S</I>)-2-(hydroxymethyl)-5-phenyl-4-[(trifluoromethylsulfonyl)oxy]tetrahydrofuran-3-ol <I>O</I>,<I>O</I>′-benzylidene derivative (<B>21</B>) by acetate, which was prepared from <B>11</B>, furnished the 2<I>S</I>,3<I>R</I>,4<I>R</I>,5<I>S</I> diastereomer <B>22</B>. The total synthesis of <B>1</B> was completed by Collins oxidation of (2<I>S</I>,3<I>R</I>,4<I>R</I>,5<I>R</I>)-2-(hydroxymethyl)-3,4-bis(methoxy-methoxy)-5-phenyltetrahydrofuran (<B>34</B>), which was prepared from <B>10</B>, and subsequent Witting olefination with (ethoxycarbonylmethylene)triphenylphosphorane followed by hydrolysis. By employing the analogous reaction sequence, compounds <B>11</B>, <B>20</B>, and <B>22</B> were efficiently converted into (+)-7,8-di-<I>epi</I>- (<B>2</B>), (+)-7-<I>epi</I>- (<B>3</B>), and (+)-8-<I>epi</I>-altholactone (<B>4</B>), respectively. The cytotoxicity of <B>1</B>–<B>4</B> against several tumor cell lines was examined.
- 公益社団法人 日本化学会の論文
著者
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Ogawa Seiichiro
Department Of Applied Cemistry Faculty Of Science And Technology Keio University
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Mclaughlin Jerry
Department Of Medicinal Chemistry And Pharmacognosy School Of Pharmacy And Pharmacal Sciences Purdue
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Tadano Kin-ichi
Department Of Applied Chemistry Faculty Of Science And Technology Keio University
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Alkofahi Ahmad
Department Of Medicinal Chemistry And Pharmacognosy Faculty Of Pharmacy Jordan University Of Science
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McLaughlin Jerry
Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy and Pharmacal Science, Purdue Unviversity
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Ueno Yoshihide
Department of Applied Chemistry, Faculty of Science and Technology, Keio University
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Alkofahi Ahmad
Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy and Pharmacal Science, Purdue Unviversity
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