The revised structure of dispermol and total synthesis of maytenoquinone, dispermol, and dispermone.
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概要
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Condensation of β-cyclocitral with 2-isopropyl-3,4-dimethoxybenzyl chloride afforded an alcohol (<B>15</B>) which was converted into (±)-12,13-dimethoxytotara-8,11,13-trien-6-one (<B>18</B>). Demethylation of (±)-<B>18</B> followed by air oxidation gave (±)-maytenoquinone. Reductive cleavage of the hydroxyl group in (±)-<B>15</B> produced a phenethyl derivative which was cyclized to give (±)-12,13-dimethoxytotara-8,11,13-triene (<B>23</B>) and its <I>cis</I>-isomer (<B>24</B>). Oxidation of (±)-<B>23</B> with chromium trioxide, followed by demethylation of the resulting 7-oxo compound (<B>25</B>), afforded (±)-dispermone. The Wittig reaction of (<I>R</I>)-(−)-α-cyclocitral with 2-isopropyl-3,4-dimethoxybenzyltriphenylphosphonium chloride yielded a styrene derivative. This was partially hydrogenated and then cyclized to give (+)-<B>23</B> and (−)-<B>24</B>. The <I>trans</I>-isomer (<B>23</B>) was converted into (−)-dispermone (<B>3</B>) <I>via</I> (−)-<B>25</B> and also partially demethylated to (+)-12-methoxytotara-8,11,13-trien-13-ol (<B>2</B>), the proposed structure for dispermol. Since the synthetic (+)-<B>2</B> was not identical with the natural compound, (−)-<B>3</B> was then converted into (+)-13-methoxytotara-8,11,13-trien-12-ol, which was identical with natural dispermol. (−)-<B>25</B> was also converted into (+)-maytenoquinone.
- 公益社団法人 日本化学会の論文
著者
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Usui Shuji
Department Of Chemistry Faculty Of Science Hiroshima University
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Matsumoto Takashi
Department of Applied Material Science, Faculty of Integrated Arts and Sciences, University of Tokushima
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Ohmura Taishi
Department of Chemistry, Faculty of Science, Hiroshima University
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