Stereocontrolled Synthesis of Adjacent Acyclic Quaternary-Tertiary Motifs: Application to a Concise Total Synthesis of (-)-Filiformin

Daniel J. Blair, Catherine J. Fletcher, Katherine M. P. Wheelhouse, Varinder K. Aggarwal*

*Corresponding author for this work

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

29 Citations (Scopus)
284 Downloads (Pure)

Abstract

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.

Original languageEnglish
Pages (from-to)5552-5555
Number of pages4
JournalAngewandte Chemie - International Edition
Volume53
Issue number22
Early online date22 Apr 2014
DOIs
Publication statusPublished - May 2014

Keywords

  • boron
  • enantioselectivity
  • lithium
  • natural products
  • total synthesis
  • REAGENT-CONTROLLED HOMOLOGATION
  • BORONIC ESTERS
  • SECONDARY ALCOHOLS
  • ENANTIOSELECTIVE CONSTRUCTION
  • STEREOSELECTIVE CONSTRUCTION
  • ELECTROPHILIC SUBSTITUTION
  • (+)-SPARTEINE SURROGATE
  • ASYMMETRIC-SYNTHESIS
  • STEREOCENTERS
  • BORYLATION

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