Total synthesis of (−)-elegansidiol by using an abnormal Beckmann fragmentation of Hajos ketone oxime as a key step

作者: Liya Cao , Jianwei Sun , Xinyan Wang , Rui Zhu , Haijian Shi

DOI: 10.1016/J.TET.2007.03.123

关键词: StereochemistryElegansidiolTotal synthesisKetoneFragmentation (cell biology)ChemistryOximeOrganic chemistryBiochemistryDrug discovery

摘要: Abstract Abnormal Beckmann fragmentation of Hajos ketone oxime regioselectively forms a chiral 1-oxygenated 2,2-dimethyl-4-methylene-cyclohexan skeleton. Using this transformation as key step, the total synthesis (−)-elegansidiol, an oxygenated mono-carbocyclic sesquiterpenoid, was achieved.

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