手性 Cermizine D 的便捷对映选择性合成。
Expedient enantioselective synthesis of cermizine D.
机构信息
Department of Chemistry, 153 Gilbert Hall, Oregon State University, Corvallis, Oregon 97331, United States.
出版信息
Org Lett. 2012 Mar 16;14(6):1596-9. doi: 10.1021/ol300342n. Epub 2012 Feb 28.
Abstract
An efficient enantioselective synthesis of cermizine D has been developed that exploits the use of a common intermediate to access over 85% of the carbon backbone. Key steps include an organocatalyzed heteroatom Michael addition, a diastereoselective alkylation with α-iodomethyl phenyl sulfide, a conjugate addition to a vinyl sulfone species, and a sulfone coupling/desulfurization sequence to join the two major subunits.
摘要
已开发出一种有效的西咪替丁 D 的对映选择性合成方法，该方法利用共同的中间体来获得超过 85%的碳骨架。关键步骤包括：有机催化的杂原子迈克尔加成、与α-碘甲基苯硫醚的非对映选择性烷基化、对乙烯砜物种的共轭加成，以及砜偶联/脱硫序列以连接两个主要的亚基。
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