An Enantioconvergent and Concise Synthesis of Losonolide A
An Enantioconvergent and Concise Synthesis of Losonolide A
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罗索内酯 A 的对映异构体简洁合成
DOI：
10.1002/anie.201811093
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发表时间：
2018
期刊：
影响因子：
--
通讯作者：
Hong Ran
中科院分区：
文献类型：
--
作者：
Yang Lin;Lin Zuming;Shao Shunjie;Zhao Qian;Hong Ran
有效获得具有重要药用价值的天然产品是药品开发的重要基础。海洋天然产品的有限供应阻碍了广泛的生物评价。尽管已经报道了（-）-lasonglyca A的几种优雅的合成，但这种有效的抗癌聚酮化合物的实际合成仍然难以捉摸。 基于硼烷作为无痕保护基的应用和前所未有的Julia烯化双砜试剂的开发，通过立体选择性硼氢化、烯丙基化和氧化，以对映收敛的方式组装（-）-lasonceptor A。 这种简洁的路线可能为获得衍生物和类似物提供一种现实的解决方案。
Efficient access to medicinally significant natural products is an essential basis for the development of pharmaceuticals. The limited availability of marine natural products impedes broad biological evaluation. Despite several elegant syntheses of (−)‐lasonolide A having been reported, a practical synthesis of this potent anticancer polyketide remains elusive. Based on the application of borane as a traceless protecting group and the development of an unprecedented bissulfone reagent for Julia olefination, (−)‐lasonolide A was assembled in an enantioconvergent manner through the application of stereoselective hydroboration, allylation, and oxidation. This concise route may provide a realistic solution for accessing derivatives and analogues.