ophiocordin has been researched along with hexahydroazepine* in 2 studies
2 other study(ies) available for ophiocordin and hexahydroazepine
| Article | Year |
|---|---|
Total synthesis of (-)-balanol, all stereoisomers, their N-tosyl analogues, and fully protected ophiocordin: an easy route to hexahydroazepine cores from garner aldehydes.
Total syntheses of (-)-balanol and all of its stereoisomers starting from easily available Garner aldehydes are described. Diastereoselective Grignard reactions on Garner aldehydes and ring-closing metatheses are the key steps for the construction of hexahydroazepine subunits. The benzophenone subunits were constructed through coupling of suitably functionalized aromatic aldehyde and bromo components. The synthetic route constitutes a convenient and scalable reaction sequence to generate all of the stereoisomers of balanol. The methodology is explored further for the synthesis of N-tosyl analogues of balanol and of fully protected ophiocordin. Topics: Aldehydes; Azepines; Hydroxybenzoates; Molecular Conformation; Stereoisomerism; Tosyl Compounds | 2008 |
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. Topics: Antifungal Agents; Azepines; Catalysis; Enzyme Inhibitors; Hydroxybenzoates; Magnetic Resonance Spectroscopy; Ruthenium Compounds | 2000 |