Peter L. Myers

Synthesis of compounds active against HIV. Part 2. Preparation of some 2′,3′-dideoxy-6′-fluorocarbocyclic nucleosides

A series of 2′,3′-dideoxy-6′-fluorocarbocyclic nucleosides have been prepared and tested for activity against HIV: compound (20) showed weak antiviral activity.

Tandem radical cyclisation ― intramolecular Mukaiyama aldolisation approach to forskolin

Abstract The trans -decalin lactone(11), an advanced intermediate towards forskolin(1), has been elaborated in five steps from the bromo-acetal(4) using a novel stereoselective intramolecular radical mediated cyclisation reaction, viz (4)→(5), in tandem with an intramolecular Mukaiyama aldolisation, viz (10)→(11).

Potent antagonists of the CCR2b receptor. Part 3: SAR of the (R)-3-aminopyrrolidine series.

SAR studies were conducted around lead compound 1 using high-throughput parallel solution and solid phase synthesis. Our lead optimization efforts led to the identification of several CCR2b antagonists with potent activity in both binding and functional assays [Compound 71 CCR2b Binding IC(50) 3.2 nM; MCP-1-Induced Chemotaxis IC(50) 0.83 nM; Ca(2+) Flux IC(50) 7.5 nM].

Synthesis of compounds active against HIV: preparation of 6′-fluorocarbocyclic AZT (AZT = 3′-deoxy-3′-azidothymidine)

The carbocyclic nucleosides (2) and (3) have been prepared and tested for anti-HIV activity: AZT-triphosphate (20)(AZT = 3′-deoxy-3′-azidothymidine) was synthesized by a new procedure and the same method was used to make the novel triphosphate (21).

Radical cyclisations onto 2(5H)-furanone and maleate electrophores leading to spiro- and linear-fused γ-lactone ring systems

Radical cyclisations involving α-acetal methyl centres and2(5H)-furanone and maleate electrophores allow the facile syntheses of spiro- and linear-fused γ-lactone ring systems e.g. (6), (10), (14) and (19), found in the ginkgolides.

2-[2-(1,4-benzodioxanyl) ]-2-imidazoline hydrochloride

Abstract A new synthesis of 2-[2-(1,4-benzodioxanyl)]-2-imidazoline hydrochloride from 2-cyano-benzodioxan is described and the previously claimed route to this compound is shown to give a formula isomer, ie. 2-methyl-2-[2-(1,3-benzodioxolyl)]-2-imidazoline hydrochloride.

Liquid phase parallel synthesis of iminodiacetic acid derivatives

Abstract Liquid phase parallel synthesis has been developed to synthesize a novel series of iminodiacetic acid derivatives targeting the integrin receptors. This library was synthesized using a four-step reaction sequence. In each step of the sequence, the PEG-bound products were precipitated selectively and the excess reagents and the by-products were removed by simple filtration. The most notable result was that the library members were obtained in high purities (>95% pure).

A stereochemically controlled intramolecular Diels–Alder approach to the octahydronaphthalene fragment of dihydromevinolin

An enantiospecific route to the octahydronaphthalene (22) from L-glutamic acid is described: the key step is the intramolecular Diels–Alder reaction (19) to (22).

The synthesis of the δ-lactone portion of the mevinic acids; a new non-acidic method of cyclic lactone expansion

An alkoxy-mercuration demercuration sequence has been used as the key step in an enantiospecific synthesis of a protected synthon for the lactone porton of the mevinic acids.

The enantiospecific synthesis of dihydromevinolin from L-glutamic acid

An enantiospecific synthesis of the diol (3), a compound which has previously been converted into dihydromevinolin, is reported.