Chemistry of insect antifeedants from Azadirachta indica (Part 17): Synthesis of model compounds of azadirachtin. Unusual effect of remote substituents on the course of the oxidative ring contraction reaction.

Robert B. Grossman, Steven V. Ley

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

The synthesis of model compounds of azadirachtin containing the tetrahydrofurancarboxylate hemiketal functional group was achieved. The course of the oxidative ring contraction reaction that was used to form this functional group was observed to be unusually sensitive to the nature of substituents remote from the reactive centre.

Original languageEnglish
Pages (from-to)11553-11568
Number of pages16
JournalTetrahedron
Volume50
Issue number39
DOIs
StatePublished - 1994

Bibliographical note

Funding Information:
Acknowledgements: We thank C. Hester Wallis and Maria-Lux de la Puente for synthetic assistance, and Drs. Andrew J. Edwards and Paul R. Raithby for the determination of the crystal stmctures. We would lie to thank the National Science Foundation for a NSF-NATO Post-Doctoral Fellowship (to RBG) and Ciba for further post-doctoral support. We also acknowledge financial support from Pfizer Central Research and the BP Research Endowment (to SVL).

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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