Beilstein J. Org. Chem.2008,4, No. 31, doi:10.3762/bjoc.4.31
synthesis of compound 22 began with double alkylation of (+)-21 through a cuprate conjugate addition followed by treatment of the resulting enolate with methyliodide (Scheme 5). Retro-Diels-Alder reaction of 22 in refluxing 1,2-dichlorobenzene gave α,β-unsaturated ketone 23. Trisubstituted cyclopentanone
Beilstein J. Org. Chem.2008,4, No. 26, doi:10.3762/bjoc.4.26
of 7a by alkylation with methyliodide, benzyl bromide, propargyl bromide, or methyl 6-O-(tolylsulfonyl)-α-D-glucopyranoside [21] afforded the thioethers 8a–d, respectively. The structural assignment of 8a–d as thioethers rest principally on their 1H and 13C NMR spectra, which contain resonances more
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Graphical Abstract
Figure 1:
The two general synthetic approaches to oxazolo[5,4-d]pyrimidines.