Citation: Jian Qiang WANG, Zhu Shou LUO, Wei Sheng TIAN. A New Asymmetric Synthesis of (+)-(3R,4S,5R,7S)-Neoclausenamide via Intramolecular Nucleophilic Attack of Carbon Anion onto Cyclic Sulfate[J]. Chinese Chemical Letters, ;1997, 8(4): 281-284. shu

A New Asymmetric Synthesis of (+)-(3R,4S,5R,7S)-Neoclausenamide via Intramolecular Nucleophilic Attack of Carbon Anion onto Cyclic Sulfate

Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032

Received Date: 17 December 1996

An intramolecular nucleophilic substitution of carbon anion to cyclic sulfate was first employed in asymmetric synthesis of (+)-(3R,4S,5R,7S)-neoclausenamide 1 which is a novel hepatoprotective lactam isolated from the dry leaves of Chinese folk medicine Clausena lansium (Lour) Skeel.The regioselectivity of β-attack to this cyclic sulfate,just like its epoxide counterpart,was attributed to the increased reactivity of β-position by the phenyl group.
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