Stereocontrol by quaternary centres: a stereoselective synthesis of (-)-luminacin D

Nathan Bartlett, Leona Gross, Florent Péron, Daniel J Asby, Matthew D Selby, Ali Tavassoli, Bruno Linclau

Research output: Contribution to journalArticle (Academic Journal)

7 Citations (Scopus)

Abstract

Very high diastereoselectivity can be achieved by 1,3-chelation-controlled allylation of aldehydes that possess a non-chelating α-ether substituent, even if the α-position is a quaternary centre and/or a spiro-epoxide. This reaction was used as a key step in an enantioselective synthesis of the angiogenesis inhibitor luminacin D.

Original languageEnglish
Pages (from-to)3306-10
Number of pages5
JournalChemistry - A European Journal
Volume20
Issue number12
DOIs
Publication statusPublished - 17 Mar 2014

Keywords

  • Aldehydes
  • Benzaldehydes
  • Catalysis
  • Chelating Agents
  • Epoxy Compounds
  • Ether
  • Spiro Compounds
  • Stereoisomerism

Fingerprint Dive into the research topics of 'Stereocontrol by quaternary centres: a stereoselective synthesis of (-)-luminacin D'. Together they form a unique fingerprint.

Cite this