Synthesis of sulfamides using ring closing diene metathesis and enyne metathesis

Salim, Sofia Saima (2005) Synthesis of sulfamides using ring closing diene metathesis and enyne metathesis. University of Southampton, Doctoral Thesis.

Abstract

Metathesis-based methodology has been developed for the synthesis of a range of medicinally important heterocyclic and fluorinated scaffolds.

The ring closing metathesis (RCM) of vinyl fluorides by RCM has been found to provide a convenient route for the incorporation of fluorine into a molecule for the first time.  The methodology has been used to synthesis heterocyclic and carbocyclic vinyl fluorides in good to excellent yield, and has been extended to the RCM of vinyl chlorides and vinyl bromides.

Enyne ring closing metathesis of sulfamide-linked internal and terminal alkynes has provided a new route to various novel seven-membered cyclic sulfamides.  The substrates bearing terminal alkynes were shown to undergo selective one-pot ring closing metathesis/cross metathesis reactions with styrene or methyl acrylate.  Structurally diverse heterocyclic compounds are also synthesised via the Diels - Alder reaction of substituted 1,3-dienes or directly from the enyne substrate in a one-pot sequence.  An enyne metathesis / Diels - Alder sequence has also been developed for the synthesis of acyclic sulfamides.

A polymer supported strategy to the synthesis of cyclic sulfamides has also been developed featuring a metathesis-based cyclisation/cleavage as the key step.  Analogues of HIV protease inhibitors were synthesised using this methodology.

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