4.7 Article

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

Journal

CHEMICAL COMMUNICATIONS
Volume 48, Issue 74, Pages 9230-9232

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c2cc32176a

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Funding

  1. EPSRC [EP/G036764/1]
  2. AstraZeneca
  3. GlaxoSmithKline
  4. Novartis
  5. Pfizer
  6. Syngenta
  7. University of Bristol
  8. Royal Society

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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.

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