CHEMISTRY OF INSECT ANTIFEEDANTS FROM AZADIRACHTA-INDICA .13. ON THE USE OF THE INTRAMOLECULAR DIELS-ALDER REACTION FOR THE CONSTRUCTION OF TRANS-FUSED HYDROBENZOFURAN FRAGMENTS FOR AZADIRACHTIN SYNTHESIS

H C KOLB, S V LEY, R N SHEPPARD, A M Z SLAWIN, S C SMITH, D J WILLIAMS, A WOOD

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10 Citations (Scopus)

Abstract

This paper describes a detailed analysis of the influence of various substituents on the stereochemical outcome of the intramolecular Diels-Alder cyclisation of a number of ether-linked trienes. In particular, the role of diene planarity in governing reaction synchronicity and related twist asynchronicity is delineated. Additionally, the controlling influence of a large dimethyl(phenyl)silyl substituent on the dienophile portion of the triene is also explored. A detailed transition-state analysis is given together with X-ray structures for compounds 41 and 46.

Original languageEnglish
Pages (from-to)2763-2777
Number of pages15
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number21
Publication statusPublished - 7 Nov 1992

Keywords

  • STEREOCHEMICAL ASPECTS
  • NMR

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