Tandem Allylboration–Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (−)-Clavosolide A

Alba Millan Delgado, James R Smith, Jack L Chen, Varinder K Aggarwal*

*Corresponding author for this work

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

34 Citations (Scopus)
422 Downloads (Pure)

Abstract

Tetrahydropyrans are common motifs in natural products and have now been constructed with high stereocontrol through a three-component allylboration-Prins reaction sequence. This methodology has been applied to a concise (13 steps) and efficient (14 % overall yield) synthesis of the macrolide (−)-clavosolide A. The synthesis also features an early stage glycosidation reaction to introduce the xylose moiety and a lithiation-borylation reaction to attach the cyclopropyl-containing side chain.
Original languageEnglish
Pages (from-to)2498-2502
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number7
Early online date14 Jan 2016
DOIs
Publication statusPublished - 12 Feb 2016

Structured keywords

  • BCS and TECS CDTs

Keywords

  • Allylboration
  • Lithiation-borylation
  • Natural products
  • Prins reaction
  • Total synthesis

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