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Cycloaddition of cyclohexa-2,4-dienones, ring-closing metathesis, and photochemical reactions: A common stereoselective approach to duprezianane, polyquinane and sterpurane frameworks

Authors
  • SINGH, V
  • PRAVEENA, GD
  • KARKI, K
  • MOBIN, SM
Publication Date
Jan 01, 2007
Source
DSpace at IIT Bombay
Keywords
Language
English
License
Unknown
External links

Abstract

A novel approach to three different types of carbocyclic frameworks belonging to dupreziananes, sterpuranes, and polyquinanes from simple aromatic precursors has been presented. Cycloaddition of appropriately appended cyclohexa-2,4-dienones with acyclic dienes gave bridged bicyclic octanes suitably disposed with olefinic chains, which upon ring-closing metathesis led to functionalized tricyclo[5.2.2.0(1,5)]undecanes related to dupreziananes. Photochemical sigmatropic 1,2- and 1,3-acyl shifts in tricyclo[5.2.2.0(1,5)] undecanes upon triplet and singlet excitation provided stereoselective routes to sterpurane and polyquinane frameworks.

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