Preparation of syn-delta-hydroxy-beta-amino esters via an intramolecular hydrogen bond directed diastereoselective hydrogenation. Total synthesis of (3S,4aS,6R,8S)-hyperaspine.
Hydrogenation of delta-hydroxy-beta-ketoester-derived enamines 8 produces syn-delta-hydroxy-beta-amino esters 9 diastereoselectively, which may be directed by the formation of an intramolecular hydrogen bond between the delta-hydroxyl and beta-amino groups. By using this method and a Dieckmann reaction as the key steps, (3S,4aS,6R,8S)-hyperaspine, a new type of ladybird alkaloid, is synthesized. [reaction: see text]
Zhu
Wei
W
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Ma
Dawei
D
D000818:Animals; D001517:Coleoptera / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D006860:Hydrogen Bonding; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D012997:Solvents; D013237:Stereoisomerism
D004952:Esters; D007202:Indicators and Reagents; D012997:Solvents