The intramolecular nucleophilic 1,5-O-heterocyclization of (η4-dienyl)-tricarbonyliron diols: Conformationally locked phosphocholines

Alain Braun, Jean Paul Lellouche

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

The 1,5-nucleophilic intramolecular O-heterocyclization of ψ-exo-/ψ-endo-(η4-dienyl)tricarbonyliron diols occurs under acid catalysis with a 1,2-migration of the complexation site. This cyclization proved to be stereoselective and provided a synthetically useful entry to novel conformationally locked alkylphosphocholines as potential anticancer agents.

Original languageEnglish
Pages (from-to)727-730
Number of pages4
JournalTetrahedron Letters
Volume43
Issue number4
DOIs
StatePublished - 21 Jan 2002

Bibliographical note

Funding Information:
The authors are grateful to Drs. Yves Rolland, René Grée and Charles Mioskowski for their interest during this work. A.B. thanks the Servier Institute (Suresnes) for its financial support through a research fellowship.

Keywords

  • (η-dienyl)tricarbonyliron(+1) cations
  • 1,5-nucleophilic substitution
  • Anticancer alkylphospholipids
  • Intramolecular O-heterocyclization

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