Claisen-rearrangement-mediated ring contraction of macrocyclic lactones. A new approach to carbocycles and heterocycles

Raymond L. Funk, Matthew M. Abelman, John D. Munger

Research output: Contribution to journalArticlepeer-review

53 Scopus citations

Abstract

Macrocyclic ketene acetals 3 undergo Claisen rearrangements smoothly and constitute a viable and general approach to hetero- or carbocyclic ring systems 4. This novel ring contraction process is subject to high internal asymmetric induction (cf. lactones 7 → carbocycles 8) as well as relative asymmetric induction in the rearrangements of ketene acetals derived from lactones 18, 23 and 27. Finally, N-benzoylmeroquinene methyl ester (37) was prepared to demonstrate the potential of this methodology in heterocycle synthesis.

Original languageEnglish (US)
Pages (from-to)2831-2846
Number of pages16
JournalTetrahedron
Volume42
Issue number11
DOIs
StatePublished - 1986

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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