An efficient synthesis of open chain nitroalcohols by regioselective ring opening of cyclic tert-#beta#-nitroalcohols by sodium borohydride: Short synthesis of (+-)-tridecan-12-olide and (+-)-9-tetradecanolide

摘要

It has been demonstrated that a wide variety of cyclic tert-#beta#-nitroalcohols can be efficiently cleaved regioselectively using stoichiometric amount of NaBH_4 in organic solvents like dry MeOH, Et_2O, CH_3CN etc. giving open chain secondary nitroalcohols such as RCH(OH)(CH_2)_nCH_2NO_2 where R is alkyl,aryl etc. and n=4,5, etc. The utility of this reaction has been demonstrated by achieving short asntheses of naturally occurring (+-)-tridecan-12-olide and (+-)-9-tetradecanolide.