Combining two-directional synthesis and tandem reactions. Part 21: Exploitation of a dimeric macrocycle for chain terminus differentiation and synthesis of an sp3-rich library

Thomas E. Storr, Sarah J. Cully, Michael J. Rawling, William Lewis, Daniel Hamza, Geraint Jones, Robert A. Stockman

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

The application of a tandem condensation/cyclisation/[3+2]-cycloaddition/elimination reaction gives an sp3-rich tricyclic pyrazoline scaffold with two ethyl esters in a single step from a simple linear starting material. The successive hydrolysis and cyclisation (with Boc anhydride) of these 3-dimensional architectures, generates unprecedented 16-membered macrocyclic bisanhydrides (characterised by XRD). Selective amidations could then be achieved by ring opening with a primary amine followed by HATU-promoted amide coupling to yield an sp3-rich natural product-like library.
Original languageEnglish
Pages (from-to)2621-2628
Number of pages8
JournalBioorganic & Medicinal Chemistry
Volume23
Issue number11
Early online date29 Dec 2014
DOIs
Publication statusPublished - 1 Jun 2015

Keywords

  • sp3-rich
  • Natural product-like
  • Scaffold
  • Cycloaddition
  • Two-directional
  • Macrocycle
  • Library
  • Tandem

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