Perry T. Kaye

Fig volatiles: Their role in attracting pollinators and maintaining pollinator specificity

Each fig tree species (Ficus) is totally dependent on a specific species of wasp for pollination and the larvae of these wasps only develop in the ovules of their specificFicus host. Because the fig crop on any particular tree is generally highly synchronized, the shortlived female wasps must leave their natal tree in order to find figs which are suitable for oviposition. Chemical volatiles produced by figs when they are ready for pollination are thought to be the means by which the wasps detect a suitable host. Gas chromatograms of the fig volatiles of 7 species ofFicus showed them to be species specific. Age related changes in the volatile profiles were noted as extra volatiles are produced when the figs were ready for pollination.

A kinetic and mechanistic study of the Baylis-Hillman reaction

Abstract Reactions of acrylate esters with pyridinecarboxaldehydes, in the presence of 3-hydroxy-quinuclidine or 1,4-diazabicyclo[2.2.2] octane, have been followed by 1H NMR spectroscopy, and a mechanism which accommodates the kinetic data hase been presented.

Does the DABCO-catalysed reaction of 2-hydroxybenzaldehydes with methyl acrylate follow a Baylis–Hillman pathway?

Evidence is presented which supports the intermediacy of dipolar Baylis-Hillman-type adducts in the synthesis of coumarin and chromene derivatives from the reaction of 2-hydroxybenzaldehydes with methyl acrylate in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO).

Synthesis and evaluation of coumarin derivatives as potential dual-action HIV-1 protease and reverse transcriptase inhibitors

Baylis-Hillman-derived 3-(benzylaminomethyl)coumarins have been treated, sequentially, with chloroacetyl chloride and propargylamine to afford alkynylated coumarins as substrates for Click Chemistry reactions with azidothymidine (AZT) in the presence of a Cu(I) catalyst. The dual-action HIV-1 protease (PR) and reverse transcriptase (RT) inhibition potential of the resulting N-benzylated cycloaddition products, and a series of non-benzylated analogues, has been explored using saturation transfer difference (STD) NMR, computer modelling and enzyme inhibition techniques.

Novel Heterocyclic Analogues of the HIV‐1 Protease Inhibitor, Ritonavir

Abstract Hydroxyethylene dipeptide isosteres containing chromone, coumarin, chromene, and thiochromene moieties have been prepared as novel analogues of the human immunodeficiency virus (HIV)‐1 protease inhibitor, ritonavir.

The Baylis–Hillman approach to quinoline derivatives

Baylis-Hillman reactions of 2-nitrobenzaldehydes with various activated alkenes afford adducts that undergo reductive cyclisation to quinoline derivatives. The chemo- and regioselectivity of cyclisation appears to be influenced by the choice of both the substrate and the reagent system, and competing reactions have been observed.

Dabco-Catalysed Reactions of Salicylaldehydes with Acrylate Derivatives

Abstract Treatment of salicylaldehydes with acrylate derivatives in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) has been shown to afford both coumarin and chromene derivatives, and factors influencing the product distributions have been investigated.

Benzodiazepine Analogues. Part 15.1 Synthesis of Benzoxathiepine Derivatives

Abstract Stepwise cyclisation sequences have provided access to a series of novel 4-phenyl-3, 4-dihydro-1,5-benzoxathiepine-2-ones and 2-and 3-phenyl-4, 1-benzoxathiepine analogues.

Necic acid synthons. Part 5. Total synthesis of (±)-retronecic acid and related compounds via zinc-mediated coupling of halogeno-esters

Zinc-mediated coupling of suitably substituted halogeno esters affords access to (±)-retronecic acid (2) and related intermediates. These approaches lead to racemic retronecic acid on the one hand and to a diastereoisomeric mixture of the acid on the other.

Application of Baylis–Hillman Methodology in the Synthesis of Coumarin Derivatives

Abstract A general, chemoselective approach to 3-substituted coumarins via Baylis–Hillman reactions of O-benzylated salicylaldehyde precursors has been demonstrated. Competitive cyclization to chromene derivatives is inhibited by conjugate addition of benzylamine or piperidine to the α,β-unsaturated ester intermediates.