Professor L.H. BriggsDr P.S. RutledgeBartley, John Peter2009-05-012009-05-011969Thesis (PhD--Chemistry)--University of Auckland, 1969.http://hdl.handle.net/2292/4233Restricted Item. Print thesis available in the University of Auckland Library or may be available through Interlibrary Loan.Attempts have been made to transform lanosterol, by both chemical and microbial means, into compounds of potential pharmacological importance. In part I some compounds with heterocyclic rings (pyrazoles, isoxazoles, and furazans) fused to ring-A have been synthesized by chemical methods. These have been tested for cytotoxic properties against lymphoid leukemia L-1210. The equilibria and n.m.r. spectra of some formyl ketones have also been studied. In part II attempts have been made to oxidize some lanosterol derivatives with microbial cultures in pursuit of synthetically useful intermediates. 3β-Hydroxy-11-keto-4, 4, 14α-trimethyl-5α-chol-8-enic acid methyl ester (35e) has been synthesized from lanosterol and transformed by Trichotecium roseum to a dihydroxy-5α-cholenic acid derivative. Extensive chemical transformations have been carried out on lanosterol to prepare substrates for microbial transformation. In particular a new efficient method for the mild degradation of the lanosterol side chain to a 17β-acetyl group has been developed.Scanned from print thesisenRestricted Item. Print thesis available in the University of Auckland Library or may be available through Interlibrary Loan.https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htmThesisFields of Research::250000 Chemical SciencesCopyright: The authorhttp://purl.org/eprint/accessRights/ClosedAccessQ112835657