化学
区域选择性
天然产物
全合成
戒指(化学)
立体化学
序列(生物学)
组合化学
有机化学
催化作用
生物化学
作者
Jan Paciorek,Denis Höfler,Kevin Rafael Sokol,Klaus Wurst,Thomas Magauer
摘要
We report a general synthetic entry to dihydrooxepine-spiroisoxazoline (DOSI) natural products that culminated in the first racemic total synthesis of psammaplysin A. For the synthesis of the unique spirocyclic fragment we employed a strategy that features two key transformations: (1) a diastereoselective Henry reaction/cyclization sequence to access the C7 hydroxylated isoxazoline scaffold in one step and (2) a regioselective Baeyer-Villiger ring expansion to install the fully substituted dihydrooxepine and avoid the risk of a previously observed oxepine-arene oxide rearrangement. The overall synthesis proceeds in 13 steps from an inexpensive starting material.
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