1344927-26-9Relevant articles and documents
Stereocontrolled synthesis of adjacent acyclic quaternary-tertiary motifs: Application to a concise total synthesis of (-)-filiformin
Blair, Daniel J.,Fletcher, Catherine J.,Wheelhouse, Katherine M. P.,Aggarwal, Varinder K.
, p. 5552 - 5555 (2014/06/10)
Lithiation/borylation methodology has been developed for the synthesis of acyclic quaternary-tertiary motifs with full control of relative and absolute stereochemistry, thus leading to all four possible isomers of a stereodiad. A novel intramolecular Zweifel-type olefination enabled acyclic stereocontrol to be transformed into cyclic stereocontrol. These key steps have been applied to the shortest enantioselective synthesis of (-)-filiformin to date (9 steps) with full stereocontrol. True to (fili)form: Lithiation/borylation methodology has been developed for the synthesis of acyclic quaternary-tertiary motifs with full control of relative and absolute stereochemistry, thus leading to all four possible isomers of a stereodiad. A novel intramolecular Zweifel-type olefination enabled acyclic stereocontrol to be transformed into cyclic stereocontrol. These key steps were applied to the enantioselective synthesis of (-)-filiformin.
Application of the lithiation-borylation reaction to the rapid and enantioselective synthesis of the bisabolane family of sesquiterpenes
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.
supporting information; experimental part, p. 9230 - 9232 (2012/09/10)
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 few
