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Oxidative cyclization of unsaturated Meldrum's acids can be carried out at temperatures as low as −30°C. The rate-determining step is cyclization of the enolate to the alkene ( 11 to 14 and 15 ) rather than enolization, which is the rate-determining step with dimethyl 4-pentenylmalonate ( 1 )....
LDA treatment of aldehydes or ketone with alkenylphosphonates 2 , prepared by Horner–Wadsworth–Emmons (HWE) reaction of methylenebisphosphonate 1 with aldehydes, afforded Baylis–Hillman reaction-type products 5 in high yields. HWE olefination of 5 with KH or KH-18-crown-6 as a base provided...
The syntheses of 2-hydroxy- N -(2-hydroxyethyl)- N , N -dimethyl-1-alkanaminium 1 ( p ) and 2-hydroxy- N , N -bis(2-hydroxyethyl)- N -methyl-1-alkanaminium 2 ( p ) bromides are described for the homologous series, tetradecanaminium ( p =14) through octadecaminium ( p =18). The critical micelle...
An efficient new route to the benzo( b )xanthone system has been developed and applied to the synthesis of several new derivatives. The cycloaddition reactions of chromone-3-carboxaldehydes 12 , reacting as dienophiles, with ortho -benzoquinodimethane 7 gave a diastereomeric mixture of...
The synthesis of racemic 7,9-dideoxythysanone 9 was achieved starting from allylnaphthalene 5 via epoxidation and reduction to bromoalcohol 7 . Subsequent lithiation of the bromide and quenching with DMF afforded lactol 8 which underwent clean oxidative demethylation to racemic...
Spirotetrahydropyridine-3-carboxylates 4 and 5 were prepared from olefins 2 and isoxazol-5-one 1 through a highly diastereoselective tandem sequential process. Three reaction workup procedures were employed, each of which afforded a different product distribution.
A catalytic asymmetric formal synthesis of 4-demethoxydaunomycin ( 3 ) was achieved using a catalytic asymmetric ring opening reaction of meso -epoxide 9 as a key step. The epoxide opening reaction was promoted by 10 mol% of Pr-( R )-BINOL–Ph 3 PO complex to give the β-amino alcohol 11 in...
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