Formal total synthesis of (-)-balanol: concise approach to the hexahydroazepine segment based on RCM.
A concise synthesis of the hexahydroazepine moiety 13 of (-)-balanol 1 is described that comprises only eight steps and is distinctly shorter than all previous reported approaches to this particular compound. Sharpless epoxidation of divinylcarbinol 4 and ring closing alkene metathesis (RCM) reaction for the formation of the heterocyclic scaffold 9 constitute the key transformations of this sequence. The latter reaction is best achieved with catalytic amounts of the ruthenium indenylidene complex 18 recently reported. Furthermore, it is demonstrated that RCM can be successfully carried out even in the presence of an azido function provided that Schrock's molybdenum alkylidene complex Mo(=NAr)(=CHCMe2Ph)[OC(Me)(CF3)2]2 (Ar = 2,6-diisopropylphenyl) is used as precatalyst.
Fürstner
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Max-Planck-Institut für Kohlenforschung, Germany.
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D000935:Antifungal Agents / Q000138:chemical synthesis; D001381:Azepines / Q000138:chemical synthesis*; D002384:Catalysis; D004791:Enzyme Inhibitors / Q000138:chemical synthesis; D062385:Hydroxybenzoates / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D017975:Ruthenium Compounds / Q000737:chemistry
D000935:Antifungal Agents; D001381:Azepines; D004791:Enzyme Inhibitors; D062385:Hydroxybenzoates; D017975:Ruthenium Compounds; C015405:ophiocordin; C048618:hexahydroazepine