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Title: Novel titanium carbenoid reagents : diversity orientated synthesis of indoles and spirocycles
Author: Main, Calver A.
ISNI:       0000 0004 2669 0767
Awarding Body: University of Glasgow
Current Institution: University of Glasgow
Date of Award: 2008
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A new synthetic strategy for the preparation of a 96-member library of 2,5-disubstituted indoles involving traceless cleavage from resin is presented. A boronate-bearing titanium alkylidene was prepared and used to convert 8 resin-bound esters into immobilised enol ethers. Cleavage from resin in mild acid with concomitant cyclisation yielded boronate-bearing indoles. Capitalising on the immobilised boronate functionality in enol ethers, Suzuki cross-coupling reactions were performed with 12 aryl iodides to give a 96-member library after cleavage from resin with mild acid, 79 members of the library were confirmed to be 2,5-disubstituted indoles. Also reported is the use of tertiary butyllithium and 2-isopropoxy-4,4,i,5-tetramethyl-l,3,2-dioxaborolane to convert an aiyl bromide into an arylboronate in the presence of a dithiane, with simultaneous reduction of an aryl azide to an amine. In a similar route, we synthesised dithiane for the attempted conversion of resin-bound esters into functionalised 7-azaindoles after cleavage from resin. Further investigation with a different ortho-nitrogen protecting group may yet prove successful.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available