Catalytic asymmetric synthesis of butane diacetal-protected (4S,5S)-dihydroxycyclohexen-1-one and use in natural product synthesis.
Catalytic asymmetric synthesis of butane diacetal-protected (4S,5S)-dihydroxycyclohexen-1-one and use in natural product synthesis.
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DOI：
10.1039/c2ob26406d
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发表时间：
2012-09
影响因子：
3.2
通讯作者：
David J. Burns;Shuji Hachisu;P. O’Brien;R. Taylor
中科院分区：
文献类型：
--
作者：
David J. Burns;Shuji Hachisu;P. O’Brien;R. Taylor
由于缺乏天然的(+)-奎宁酸作为起始原料，设计了一种六步法合成丁烷双缩醛保护的(4S,5S)-二羟基环己烯-1-酮（正式来源于(+)-奎宁酸）。关键的催化不对称步骤涉及手性共聚物催化环氧化物开环反应。利用(4S,5S)-二羟基环己烯-1- 1合成了两种环己酮天然产物。
Due to the lack of availability of unnatural (+)-quinic acid as a starting material, a 6-step synthesis of butane diacetal-protected (4S,5S)-dihydroxycyclohexen-1-one (formally derived from (+)-quinic acid) has been devised. The key catalytic asymmetric step involves a chiral Co-salen-catalysed epoxide ring-opening reaction. (4S,5S)-Dihydroxycyclohexen-1-one was utilised in the synthesis of two cyclohexenone natural products isolated from the mycelia of Lasiodiplodia theobromae.