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Dive into the research topics where David M. Hollinshead is active.

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Journal of The Chemical Society-perkin Transactions 1 | 1984

Oxo complexes of ruthenium(VI) and (VII) as organic oxidants

G. Green; William P. Griffith; David M. Hollinshead; Steven V. Ley; Martin Schröder

Oxidation of a variety of saturated and unsaturated primary and secondary alcohols by tetraoxoruthen-ate(VI), [RuO4]2–, tetraoxoruthenate(VII), [RuO4]–, barium trans-trioxodihydroxoruthenium(VI), trans-Ba[Ru(OH)2O3], dioxotrichlororuthenate(VI), [RuO2Cl3]–, and dioxodichlorobipyridylruthenate(VI), [RuO2(bipy)Cl2], has been studied; [RuO4]2–may be used catalytically in conjunction with [S2O8]2– under basic aqueous conditions. For some of these systems, the oxidation of several aldehydes and amines were also examined. Both [RuO4]2–and [RuO4]– oxidise primary alcohols to carboxylic acids and secondary alcohols to ketones; the reactivity of these reagents towards unsaturated alcohols was studied in particular. The new species [PPh4][RuO2Cl3] and also [RuO2(bipy)Cl2] cleanly oxidise a wide range of alcohols to aldehydes and ketones without attack of double bonds. Ba[Ru(OH)2O3] functions as a heterogeneous oxidant in dichloromethane, oxidising only the most reactive alcohols to aldehydes.


Journal of The Chemical Society-perkin Transactions 1 | 1983

The Diels–Alder route to drimane related sesquiterpenes; synthesis of cinnamolide, polygodial, isodrimeninol, drimenin and warburganal

David M. Hollinshead; S. Christopher Howell; Steven V. Ley; Michael Mahon; Norman M. Ratcliffe; Paul Anthony Worthington

The stereospecific preparation of various 1-vinyl-2,6,6-trimethylcyclohex-1-enes (6) as potential diene precursors in the Diels–Alder reaction with dimethyl acetylenedicarboxylate have been investigated. The reaction of the parent diene (6a) with dimethyl acetylenedicarboxylate affords an adduct (18) in 94% yield. This species was reductively isomerised using 10% Pd/C/H2 and a mineral acid to give a trans-fused decalin diester (19). Reduction of (19) with lithium aluminium hydride afforded 1,4,4a,5,6,8,8a-octahydro-5,8,8a-trimethyl-1 β,4a α,8aβ-naphthalene-1,2-dimethanol (24) a key starting material for the highly efficient syntheses of five drimane sesquiterpene natural products, cinnamolide (1), polygodial (2), isodrimeninol (3), drimenin (4), and warburganal (5). Microbial oxidation reactions using C. elegans or A. niger of (2), (24), and (1) gave good yields of the corresponding 3β-hydroxy derivatives, (30), (31), and (32). Several other unusually substituted drimane derivatives are reported.


Tetrahedron | 1984

Fe2(co)g in tetrahydrofuran or under sonochemical conditions as convenient practical routes to π-allyltricarbonyliron lactone complexes

Averil M. Horton; David M. Hollinshead; Steven V. Ley

Abstract A series of alkenyl epoxides were converted into their corresponding π-allyltricarbonyliron lactone complexes by either treatment with tetrahydrofuran solutions of Fe2(CO)9 at room temperature, or in hydrocarbon solvents with Fe2(CO)9 under ultrasonification conditions. The new routes constitute convenient practical alternatives to presently existing methodology.


Journal of The Chemical Society, Chemical Communications | 1984

π-Allyltricarbonyliron lactone complexes in synthesis: application to the synthesis of the β-lactam antibiotic (+)-thienamycin

Simon T. Hodgson; David M. Hollinshead; Steven V. Ley

Synthesis of an enantiomerically pure β-lactam intermediate used in the preparation of the antibiotic (+)-thienamycin is described, by suitable elaboration of a functionalised π-allyltricarbonyliron complex.


Journal of The Chemical Society-perkin Transactions 1 | 1985

Use of π-allyltricarbonyliron lactam complexes in the preparation of nocardicin derivatives: synthesis of (−)-3-oxo-1-[(p-benzyloxyphenyl)-benzyloxycarbonylmethyl]azetidin-2-one

Simon T. Hodgson; David M. Hollinshead; Steven V. Ley; Caroline M. R. Low; David J. Williams

A short five-step synthesis, in 79% overall yield, of (–)-3-Oxo-1 -[(p-benzyloxyphenyl) benzyloxy-carbonylmethyl]azetidin-2-one (3), a precursor for nocardicin synthesis has been developed from isoprene monoepoxide. The key steps of the procedure rely on the efficient transformation of 2–4-η3-(1-formyloxy-2-methylbut-3-en-2-ylato)tricarbonyliron into the corresponding diastereoisomeric lactam complexes (6) and (7) using D-(–)-benzyl-(p-benzyloxyphenyl)glycinate (5) and ZnCl2·TMEDA (TMEDA = tetramethylethylenediamine), and their oxidation with ceric ammonium nitrate to 3-isopropenylazetidinone derivatives.


Journal of The Chemical Society-perkin Transactions 1 | 1983

Synthesis of ?-lactams from ?-allyltricarbonyliron (lactone) complexes

G. D. Annis; Elizabeth M. Hebblethwaite; Simon T. Hodgson; David M. Hollinshead; Steven V. Ley

Several π-allyltricarbonyliron (lactone) complexes have been treated with an excess of benzylamine in the presence of Lewis acids to afford the corresponding lactam complexes by an SN2′-like process. These lactam complexes were oxidised in good yield with ceric ammonium nitrate to provide a novel route to a variety of β-lactam compounds. Simple chemical transformations of the resulting β-lactams have been investigated; these include the conversion of the vinyl and isopropenyl side chains into hydroxyethyl substituents and the reductive removal of benzyl groups to afford the parent NH β-lactams.


Journal of The Chemical Society-perkin Transactions 1 | 1981

Dissolving metal reduction of esters to alkanes. A method for the deoxygenation of alcohols

Anthony G. M. Barrett; Christopher R. A. Godfrey; David M. Hollinshead; Panayiotis A. Prokopiou; Derek H. R. Barton; Robin B. Boar; Laurette Joukhadar; James F. McGhie; Satish C. Misra

Diverse carboxylic esters have been reduced with dissolving Group 1A metals. Using lithium in ethylamine, sterically hindered esters (RCO2R′) were deoxygenated giving the alkane (R′H) whereas non-hindered esters regenerated the parent alcohol (R′OH). This permitted the selective deoxygenation of diesters. Conversely, potassium–sodium eutectic solubilised with 18-crown-6 in t-butylamine and tetrahydrofuran (THF) efficiently deoxygenated both hindered and non-hindered esters. In the absence of nucleophiles at ambient temperature the principal reaction of carboxylic ester radical anions was deoxygenation.


Journal of The Chemical Society-perkin Transactions 1 | 1983

Synthesis of β-lactams from π-allyltricarbonyliron (lactone) complexes

G. D. Annis; Elizabeth M. Hebblethwaite; Simon T. Hodgson; David M. Hollinshead; Steven V. Ley


Synthesis | 1993

Dispiroketals in Synthesis (Part 3):1Selective Protection of Diequatorial Vicinal Diols in Carbohydrates

Steven V. Ley; Geert-Jan Boons; Ray Leslie; Martin Woods; David M. Hollinshead


ChemInform | 1986

Use of π-Allyltricarbonyliron Lactam Complexes in the Preparation of Nocaridicin Derivatives: Synthesis of (-)-3-Oxo-1-[(p-benzyloxyphenyl)benzyloxycarbonylmethyl]azetidin-2-one.

Simon T. Hodgson; David M. Hollinshead; Steven V. Ley; C. M. R. Low; David J. Williams

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G. Green

Imperial College London

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Christopher R. A. Godfrey

Institut de Chimie des Substances Naturelles

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