Total Synthesis of Diospyrodin and Its Three Diastereomers
Total Synthesis of Diospyrodin and Its Three Diastereomers
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薯蓣皂苷及其三种非对映体的全合成
DOI：
10.1021/acs.orglett.0c02280
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发表时间：
2020
期刊：
影响因子：
5.2
通讯作者：
Inoue Masayuki
中科院分区：
文献类型：
--
作者：
Fukuda Takumi;Nagatomo Masanori;Inoue Masayuki
经13步反应合成了具有抗菌活性的二烯吡罗啶（1）。Et 3B和O2促进l-核糖衍生的α-烷氧基酰基碲5与d-葡萄糖衍生的碲4反应生成α-烷氧基碳自由基。自由基加成实现了3-α连续羟基碳链的聚合组装，大大简化了合成路线。化合物3-α不仅转化为1，而且通过官能团操作转化为它的三个非对映体。
Antibacterial diospyrodin (1) was synthesized in 13 steps. Et3B and O2promoted the formation of an α-alkoxy carbon radical froml-ribose-derived α-alkoxyacyl telluride5, which reacted withd-glucose-derived aldehyde4. The radical addition realized the convergent assembly of the contiguously hydroxylated carbon-chain of3-αand greatly contributed to streamlining the synthetic route. Compound3-αwas transformed not only to1but also to its three diastereomers by functional group manipulations.