Application of the lithiation–borylation reaction to the rapid and enantioselective synthesis of the bisabolane family of sesquiterpenes

…, MJ Hesse, BM Partridge, P Roth, SP Thomas…

Index: Aggarwal, Varinder K.; Ball, Liam T.; Carobene, Simon; Connelly, Rickki L.; Hesse, Matthew J.; Partridge, Benjamin M.; Roth, Philippe; Thomas, Stephen P.; Webster, Matthew P. Chemical Communications, 2012 , vol. 48, # 74 p. 9230 - 9232

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Citation Number: 12

Abstract

The expedient enantioselective synthesis of 5 bisabolane sesquiterpenes has been achieved using a common, one-pot lithiation–borylation reaction of secondary benzylic carbamates and either protodeboronation or oxidation to give the natural products in fewer than 5 steps, with high yield and> 94: 6 er.