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A gram-scale batch and flow total synthesis of perhydrohistrionicotoxin

机译：克级分批和流式全氢组氨酸毒素的全合成

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摘要

The total synthesis of the spi- ropiperidine alkaloid (-)-perhydrohis- trionicotoxin (perhydro-HTX) 2 has been accomplished on a gram scale by employing both conventional batch chemistry as well as microreactor techniques.)-6-Pentyltetrahydro- pyran-2-one 8 underwent nucleophilic ring opening to afford the alcohol 10, which was elaborated to the nitrone 13. Protection of the nitrone as the 1,3- adduct of styrene and side-chain extension to the unsaturated nitrile afforded a precursor 17, which underwent dipolar cycloreversion and 1,3-dipolar cycloaddition to give the core spirocyclic precursor 18 that was converted into perhydro-HTX 2. The principal steps to the spirocycle 18 have successfully been transferred into flow mode by using different types of microreactors and in a telescoped fashion, allowing for a more rapid access to the histrioni- cotoxins and their analogues by continuous processing.
机译：通过使用常规分批化学方法和微反应器技术，可以在克级完成螺哌啶生物碱（-）-全氢组-三级毒素（perhydro-HTX）2的全合成。）-6-戊基四氢吡喃-2 -一个8经历亲核开环以提供醇10，其被醇化为硝酮13。保护作为苯乙烯的1，3-加合物的硝酮和侧链延伸至不饱和腈提供了前体17，其进行了通过偶极环还原和1,3-偶极环加成反应，得到了螺线型螺环前体18，该螺线型前体18已转化为过氢HTX2。螺线环18的主要步骤已通过使用不同类型的微反应器并以伸缩方式成功地转换为流动模式，可以通过连续加工更快地获得组氨酸毒素及其类似物。

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