Showing papers by "Andrew B. Holmes published in 1989"
TL;DR: In this article, the relative stereochemistry was established by the asymmetric synthesis of trans-(2R),(9R)-dimethyloxonane (13) and meso cis-2,9-dimethyloxideonane(17), which was converted into the carbon skeleton of obtusenyne.
26 citations
TL;DR: In this paper, the enantioselective syntheses of (S)-γ-acetylacetylenic γ-aminobutyric acid (GABA) and the (E)-butenynyl analogue (2) by phthalimide displacement of the homochiral prop-2-ynylic alcohols (6) and (11)[generated from the acetals (3, and (9, respectively], are reported.
Abstract: The enantioselective syntheses of (S)-γ-acetylenic γ-aminobutyric acid (GABA)(1) and the (E)-butenynyl analogue (2) by phthalimide displacement of the homochiral prop-2-ynylic alcohols (6) and (11)[generated from the acetals (3) and (9), respectively], are reported.
13 citations
TL;DR: In this article, the peracetic acid degradation of 1-methoxybicyclo[2.2]oct-5-enones (4a-f) was studied.
7 citations
TL;DR: In this article, Lewis acid catalysed cycloaddition of the dienes to 2-chloroacrylonitrile occurs in high yield and with stereoselectivity to give the corresponding adducts, which can be rearranged upon treatment with fluoride ion to the bicyclic cyclohexenones.
2 citations
TL;DR: In this paper, the racemates of indolizidine 167B (X), 205A (XVI), and 207A(XVII) as well as (-)-indolizzidine 209B (XXVI) are prepared as shown using a general strategy.
Abstract: The racemates of indolizidine 167B (X), 205A (XVI) and 207A (XVII) as well as (-)-indolizidine 209B (XXVI) are prepared as shown using a general strategy.
1 citations
TL;DR: The reaction of the N-tosyl imino-ester (1) with 2-trimethylsilyloxycyclohexadiene (2) followed by acidic work-up shows a divergence in pathways: at low temperature in polar solvents the cyclohexenones (5) and (6)(X-ray) are favoured, whereas at higher temperatures the bicyclic ketones (3) and X-ray are the predominant products as mentioned in this paper.
Abstract: The reaction of the N-tosyl imino-ester (1) with 2-trimethylsilyloxycyclohexadiene (2) followed by acidic work-up shows a divergence in pathways: at low temperature in polar solvents the cyclohexenones (5) and (6)(X-ray) are favoured, whereas at higher temperatures the bicyclic ketones (3) and (4)(X-ray) are the predominant products.