Oxazoline N-oxide-mediated [2+3] cycloadditions. Application to a synthesis of (-)-tetrahydrolipstatin.
[reaction: see text] A [2+3] cycloaddition of camphor-derived oxazoline N-oxide to alpha,beta-unsaturated ester afforded adduct 8. Tetrahydrolipstatin 1 was prepared from this compound in a nine-step sequence of reactions.
Dirat
O
O
Laboratoire de Synthèse des Substances Naturelles, Associé au CNRS, ICMO, Bâtiment 410, Université de Paris-sud, 91405 Orsay, France.
Kouklovsky
C
C
Langlois
Y
Y
D000447:Aldehydes; D003500:Cyclization; D006868:Hydrolysis; D007202:Indicators and Reagents; D007783:Lactones / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D000077403:Orlistat; D010080:Oxazoles / Q000737:chemistry*; D010084:Oxidation-Reduction
D000447:Aldehydes; D007202:Indicators and Reagents; D007783:Lactones; D010080:Oxazoles; D000077403:Orlistat