Sesquiterpene synthesis via organometallic intermediates

Johnson, Simon Adrian (1980) Sesquiterpene synthesis via organometallic intermediates. University of Southampton, Doctoral Thesis.

Abstract

An investigation has been made into the reactions of bisisoprene Ni(0)-Ligand systems with substituted acetylenes and olefins in an effort to form germacradiene systems. When phosphorus coordinating ligands were present it was found that preferential reaction of the olefin or acetylene with the ligands rather than with isoprene occurred. When 2,6-lutidine was employed as the coordinating ligand cooligomerisation was achieved, although the products did not have the required ten membered ring structure. An approach to the synthesis of furanodiene employing intramolecular attack of a nickel allyl bromide complex onto a 3-bromofuran system was investigated. This was unsuccessful because attempts to prepare the dibromide precursor by bromination of an hydroxyl function in the presence of other sensitive groups, failed. A study into the reactions of nickel allyl bromide complexes with imines was made and the possibility of intramolecular reaction to form heterocyclic systems was investigated. Finally, some studies were carried out to determine the feasibility of a palladium (0) catalysed cyclisation of a carboxylic acid on to a double bond being vied as a basis for the synthesis of Paniculide C.

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