引用本文:
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.
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.
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.
A New Asymmetric Synthesis of (+)-(3R,4S,5R,7S)-Neoclausenamide via Intramolecular Nucleophilic Attack of Carbon Anion onto Cyclic Sulfate
摘要:
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.
English
A New Asymmetric Synthesis of (+)-(3R,4S,5R,7S)-Neoclausenamide via Intramolecular Nucleophilic Attack of Carbon Anion onto Cyclic Sulfate
Abstract:
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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