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

Varinder K. Aggarwal*, Liam T. Ball, Simon Carobene, Rickki L. Connelly, Matthew J. Hesse, Benjamin M. Partridge, Philippe Roth, Stephen P. Thomas, Matthew P. Webster

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

25 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)9230-9232
Number of pages3
JournalChemical Communications
Volume48
Issue number74
DOIs
Publication statusPublished - 2012

Structured keywords

  • BCS and TECS CDTs

Keywords

  • TERTIARY BORONIC ESTERS
  • SECONDARY ALCOHOLS
  • (+)-CURCUPHENOL
  • (R)-(-)-CURCUPHENOL
  • (S)-(+)-CURCUPHENOL
  • (-)-CURCUQUINONE
  • CONVERSION
  • ROUTE
  • PROTODEBORONATION
  • METHODOLOGY

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