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A new synthesis of macrocyclic keto-lactones via ring expansion of 2-(3-hydroxypropyl)-2-nitrocycloalkanones

✍ Scribed by Richard C. Cookson; Partha S. Ray

Publisher
Elsevier Science
Year
1982
Tongue
French
Weight
183 KB
Volume
23
Category
Article
ISSN
0040-4039

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✦ Synopsis

2-(3-Hydroxypropyl)-2-nitrocycloalkanones undergo base-catalysed isomerisation into nitro-lactones containing

'Theketo-lactones 5 have been made before by oxidation of the dihydropyrans 7 to the diols with moist peractic acid followed by treatment with lead tetra-acetate or by direct oxidation with chromic or m-chloroperbenzoic acid.Theethers 7 were prepared by dehydration of the hydroxypropyl-ketones obtained either by alkylation of the pyrrolidine enamines with lacetoxy-3-bromopropane and hydrolysis or by Michael addition of the enamines to methyl acrylate and reduction with lithium aluminium hydride.

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