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DEVELOPMENT OF NEW METHODS FOR THE SYNTHESIS OF DIHYDROPYRANS AND TETRAHYDROPYRANS

Mad Nasir, Nadiah (2016) DEVELOPMENT OF NEW METHODS FOR THE SYNTHESIS OF DIHYDROPYRANS AND TETRAHYDROPYRANS. PhD thesis, University of York.

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Abstract

This thesis detail attempts to develop a procedure, based on the Maitland-Japp reaction, for the formation of functionalised tetrahydropyran (THP) rings. Previous work in the Clarke group has focused on the development of the Maitland-Japp reaction, but it produced mixtures of diastereomeric THPs. The work described in this thesis details the stereocontrolled synthesis of functionalised 2,6-cis- and 2,6-trans-THP rings from dihydropyran (DHP) rings, as well as the synthesis of 3,3,6-trisubstituted THP rings. The formation of 2,6-cis THP rings was achieved by the addition of hydride nucleophiles to C2-substituted DHPs, and trapping with carbon electrophiles. Treatment of 2H-DHPs with carbon nucleophiles led to the formation of 2, 6-trans THP rings. Reduction of 2H-DHPs with L-Selectride® produce the 3,6-disubstituted THP rings, while trapping of the intermediate enolate with carbon electrophiles give formation of 3,3,6-trisubstituted THP rings. The development of a successful method for the synthesis of functionalised THP rings led to a synthesis of the A-ring of Lasonolide A and Diospongin B.

Item Type: Thesis (PhD)
Academic Units: The University of York > Chemistry (York)
Identification Number/EthosID: uk.bl.ethos.702667
Depositing User: Mrs Nadiah Mad Nasir
Date Deposited: 31 Jan 2017 15:14
Last Modified: 24 Jul 2018 15:21
URI: http://etheses.whiterose.ac.uk/id/eprint/15960

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