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Title: Stereocontrol in the synthesis of substituted spirocyclic ethers
Author: Bird, P. M.
Awarding Body: University of Cambridge
Current Institution: University of Cambridge
Date of Award: 1997
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This thesis describes the synthesis of spirocyclic ethers with substituents in both rings. The strategy employed is considered in stepwise manner starting with the two-step synthesis of the substituted cyclic α-phenylsulfanylcarbaldehydes A and B from the corresponding cyclic ketones, paying particular attention to the stereoselectivity in the first step and the stereospecificity of the second. Simple aldol reactions of these aldehydes with ester and ketone enolates are reported, along with the conversion of the aldol products C to (1,3)-diols D by reduction (including the[1,3]-stereoselective reduction of β-hydroxyketones) or addition of an organometallic reagent. The stereospecific cyclisation of these diols to the targeted spirocyclic ethers E was achieved by treatment with catalytic amounts of p-touenesulfonic acid. Elucidation of the stereochemistry of these tetrahydrofurans and their precursors - and the implications of these assignments - by the examination of 2-D NMR spectra is discussed.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available