Regio- and Stereoselective Homologation of 1,2-Bis(Boronic Esters): Stereocontrolled Synthesis of 1,3-Diols and Sch 725674

Alexander Fawcett, Dominik Nitsch, Muhammad Ali, Joe M Bateman, Eddie L. Myers, Varinder K. Aggarwal*

*Corresponding author for this work

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

28 Citations (Scopus)
375 Downloads (Pure)

Abstract

1,2-Bis(boronic esters), derived from the enantioselective diboration of terminal alkenes, can be selectively homologated at the primary boronic ester by using enantioenriched primary/secondary lithiated carbamates or benzoates to give 1,3-bis(boronic esters), which can be subsequently oxidized to the corresponding secondary-secondary and secondary-tertiary 1,3-diols with full stereocontrol. The transformation was applied to a concise total synthesis of the 14-membered macrolactone, Sch 725674. The nine-step synthetic route also features a novel desymmetrizing enantioselective diboration of a divinyl carbinol derivative and high-yielding late-stage cross-metathesis and Yamaguchi macrolactonization reactions.

Original languageEnglish
Pages (from-to)14663-14667
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number47
Early online date11 Nov 2016
DOIs
Publication statusPublished - 14 Nov 2016

Keywords

  • 1,3-diols
  • diboration
  • homologation
  • lithiation
  • Sch 725674

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