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- Title
Synthesis of 13,14-Dehydro-15-deoxy-16-hydroxy-16-methyl-17-phenoxyprostaglandin B1 Ethyl Ester.
- Authors
Ivanova, N. A.; Shavaleeva, G. A.; Miftakhov, M. S.
- Abstract
A new synthetic route has been developed for the construction of the main skeleton of ω-aryloxyprostaglandin (PG) via 1,2-addition of lithiated 3-methyl-3-(trimethylsilyloxy)pent-1-yne to the ketone carbonyl group of ethyl 7-(5-oxocyclopent-1-en-1-yl)heptanoate. The addition reaction was accompanied by the formation of cyclopentenone dimer as minor product. The 1,2-adduct containing a tertiary hydroxy group was oxidized with pyridinium chlorochromate to 13-dehydro-PGB1 ethyl ester.
- Subjects
CARBONYL group; ADDITION reactions; ETHYL group; ETHYL esters; KETONES; SKELETON
- Publication
Russian Journal of Organic Chemistry, 2020, Vol 56, Issue 3, p540
- ISSN
1070-4280
- Publication type
Article
- DOI
10.1134/S1070428020030288