The first synthesis of the ABC-ring system of 'Upenamide
The first synthesis of the ABC-ring system of 'Upenamide
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DOI：
10.1021/ol701772d
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发表时间：
2007-09-27
期刊：
影响因子：
5.2
通讯作者：
Taylor, Richard J. K.
中科院分区：
文献类型：
--
作者：
Schmidt, Jan Peter;Beltran-Rodil, Sandra;Taylor, Richard J. K.
大环海洋生物碱'upenamide (1) 的螺恶喹啉齐啶酮核心（ABC 核心）的第一个合成路线已经开发出来。所有五个立体中心均具有完整的立体控制功能。 C-11 处的羟基是通过区域选择性和立体选择性 SeO2 介导的烯丙基氧化引入的。螺环骨架是通过氯化亚锡诱导的脱缩醛化-双环化过程形成的。通过酶促去对称化和掺入 (S)-苹果酸衍生结构单元引入了更多立体中心。
The first synthetic route to the spirooxaquinolizidinone core (ABC core) of the macrocyclic marine alkaloid 'upenamide (1) has been developed. All five stereocenters were introduced with complete stereocontrol. The hydroxyl group at C-11 was introduced by a regio- and stereoselective SeO2-mediated allylic oxidation. The spirocyclic skeleton was formed by a stannous chloride induced deacetalization-bicyclization procedure. Further stereocenters were introduced by an enzymatic desymmetrization and by incorporation of an (S)-malic acid derived building block.