Charles M. Marson

Synthesis of polysubstituted thiophenes by a catalytic cyclisation of functionalised episulfides

Abstract Substituted thiophenes are formed by the reaction of 1-alkynyl-2,3-epithioalcohols with a catalytic amount of mercury II prepared from HgO and dilute sulfuric acid.

Construction of polyfunctionalized seven-membered rings by the cyclization of 2,3-epoxy alcohols

Abstract Acetylenic epoxy alcohol cyclizations provide an efficient stereocontrolled construction of functionalized, dihydroxylated cycloheptanoid ring systems.

Stereocontrolled routes to bridged ethers by tandem cyclizations

Ring contraction of a 3,4-epoxyalcohol, then lactolization and electrophilic attack are the steps in the domino cyclization protocol for the formation of 8-oxabicyclo[3.2.1]octane systems [Eq. (a)].

A sequential stereocontrolled cyclopropane ring formation and semi-pinacol rearrangement

Treatment of an unsaturated 2,3-epoxy alcohol with SnBr 4 leads to a stereoselective formation of a cyclopropane ring, and an α-ketol unit as part of a subsequent ring expansion.

Highly efficient syntheses of 3-aryl-2-cycloalken-1-ones and an evaluation of their liquid crystalline properties

Cycloalkenones are shown to be mesogens and can be synthesised in near quantitative yields by a convergent palladium(0)-catalysed cross-coupling strategy; a 2-methyl group induces a change of phase from smectic to nematic.

Total synthesis of the naturally occurring furanoid fatty acid, F5

The furanoid fatty acid Fg has been synthesized using a mercury(II) catalyzed isomerization of 2-(1,2-oxiranylcyclododecyl)-3-nonyn-2-ol

Convergent stereocontrolled construction of 5-7-6 tricyclic aza analogues of phorbol and aconite alkaloids

Abstract An acyliminium cyclization is used to construct the central seven-membered ring of 5-7-6 tricyclic aza-analogues of diterpenoids.

Tin (IV)-mediated stereoselective synthesis of epoxides with concomitant alkyl peroxide formation

Abstract Epoxy alkyl peroxides are formed stereoselectively by the action of t -butyl hydroperoxide-SnCl 4 upon allylic alcohols containing an amido group, and with reversal of the diastereoselectivity shown by the action of t -butyl hydroperoxide-VO(acac) 2 upon analogous carbocyclic alcohols.

Synthesis of γ-hydroxy α,β-unsaturated amides by base-induced isomerization of epoxy amides

Treatment of 3,4-epoxyamides with LDA affords γ-hydroxy-α,β-unsaturated amides, usually with high (E)-selectivity. The 3,4-epoxyamides were prepared by the epoxidation of β,γ-unsaturated amides with meta-chloroperbenzoic acid.

Regioselective 2H-3,6-dihydropyran synthesis with tandem oxo-ene formalism

Abstract Condensation of 3-alkenamides with s -trioxane in the presence of trifluoromethanesulfonic acid affords 2 H -3,6-dihydropyrans.