Marie L. Smith

Carbon based nucleophilic ring opening of activated monocyclic β-lactams; Synthesis and stereochemical assignment of the ACE inhibitor WF-10129

Abstract The preparation of γ-keto α-amino acids via carbon based nucleophilic ring opening of activated monocyclic β-lactams was examined and applied to the synthesis and stereochemical assignment of the dipeptide angiotensin converting enzyme (ACE) inhibitor, WF-10129.

ENANTIOSPECIFIC SYNTHESIS OF (3R, 4R)-3-AMINO-1-HYDROXY-4-METHYL PYRROLIDIN-2-ONE (L-687,414), AN NMDA RECEPTOR ANTAGONIST

Abstract An enantiospecific synthesis of the NMDA receptor antagonist (3R, 4R)-3-amino-1-hydroxy-4-methylpyrrolidin-2-one via ring opening of the chiral β-lactam (9) is reported.

Impurity annihilation; a strategy for solution phase combinatorial chemistry with minimal purification

The selective annihilation of all contaminants in the solution phase formation of amides or sulfonamides is accomplished by their incorporation into a polyurea and removal by filtration.

Chameleon catches in combinatorial chemistry: Tebbe olefination of polymer supported esters and the synthesis of amines, cyclohexanones, enones, methyl ketones and thiazoles

Tebbe olefination of supported esters R1CO2CH2–polymer gave the corresponding vinyl ethers R1C(CH2)OCH2–polymer which were released, under acidic conditions, to produce methyl ketones R1COMe; by reductive amination, to produce amines R1CH(Me)NHR2; by bromination and reaction of R1CBr(CH2Br)OCH2-polymer with thioureas to produce thiazoles; or, for supported dienyl ethers derived from α,β-unsaturated esters, by Diels–Alder reaction and acid mediated cleavage to produce cyclohexanone derivatives.

The total synthesis of (±)-trichoviridin

The total synthesis of (±)-trichoviridin, a naturally occurring epoxy-isonitrile, is described.

Polymer backbone disassembly: polymerisable templates and vanishing supports in high loading parallel synthesis

In the synthesis of a library of N-alkyl-3-aza-8-oxabicyclo[3.2.1]octane-6,7-dimethanol derivatives, prepared from an 7-oxabicyclo[2.2.1]hept-2-ene-5,6-dimethanol derivative via ring opening metathesis polymerisation using Cl2(Cy3P)2RuCHPh, selective alkylation, ozonolytic scission of the polymer backbone and reductive alkylation, purification was facilitated by the differential solubility of the polymer intermediates.

Total synthesis of (+)-pramanicin and stereochemical elucidation of the natural product

Total synthesis of (+)-pramanicin is achieved through a ‘one pot’ Michael addition of an aminosilyl zincate species to an α,β-unsaturated lactam and quenching of the resultant enolate with an α,β-unsaturated γ,δ-epoxy aldehyde.