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Alkenyl sulphoxides as precursors to cyclopentenones and prostanoid β-side chains

✍ Scribed by Peter J. Brown; D.Neville Jones; M.Akram Khan; Nicholas A. Meanwell


Book ID
104216931
Publisher
Elsevier Science
Year
1983
Tongue
French
Weight
235 KB
Volume
24
Category
Article
ISSN
0040-4039

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✦ Synopsis


Conjugate additions of enolate anions to a,B-unsaturated sulphoxides follcwed by sulphoxide-ketone transformations provided simple syntheses of cyclopentenones, and 2-phenylsulphinyloct-I-en-3-one provided a convenient electrophilic prostanoid B-side chain precursor.


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## Abstract The benzoylated Corey aldehyde 1a can be alkynylated with hept‐1‐ynyl‐triisopropoxytitanium in good chemical yield and high diastereoselectivity to the (R)‐alcohol 3c admixed with about 10% of the diastereomeric (S)‐alcohol 2c. Without removal of this admixture the (R)‐alcohol 3c was co