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.
Srivastava
Ajay Kumar
AK
Medicinal and Process Chemistry Division, Central Drug Research Institute, Lucknow, UP, India.
Panda
Gautam
G
D000447:Aldehydes / Q000737:chemistry*; D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D062385:Hydroxybenzoates / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism; D014105:Tosyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000447:Aldehydes; D001381:Azepines; D062385:Hydroxybenzoates; D014105:Tosyl Compounds; C015405:ophiocordin; C048618:hexahydroazepine