Open AccessTransformations of 3,7-interphenylene 11-deoxyprostanoid formyl precursors in the acidic medium
Author(s) -
Felix S. Pashkovsky,
Д. И. Корнеев,
Ф. А. Лахвич
Publication year - 2021
Publication title -
doklady nacionalʹnoj akademii nauk belarusi
Language(s) - English
Resource type - Journals
eISSN - 2524-2431
pISSN - 1561-8323
DOI - 10.29235/1561-8323-2021-65-6-702-707
Subject(s) - chemistry , substituent , acetal , hydrolysis , synthon , naphthalene , alkoxy group , isomerization , disproportionation , stereochemistry , hydroxymethyl , medicinal chemistry , organic chemistry , catalysis , alkyl
It has been shown that the formyl precursors of 3,7-interphenylene 11-deoxyprostanoids, formed during acidic hydrolysis of the corresponding acetals, can undergo isomerization (disproportionation) in the acidic medium to give 2-(arylalkyl)-3-(hydroxymethyl)cyclopent-2-ene-1-ones – the synthons for prostanoids and phytoprostanes of the series B. Acetal precursors of 3,7-interphenylene 11-deoxyprostaglandin analogues with electron-donating alkoxy substituent in position 3′ of the aromatic fragment in the α-chain under similar conditions hydrolyze with the formation of formyl derivatives that spontaneously cyclize to produce 2,3,4,9-tetrahydro-1H-cyclopenta[b]naphthalene-1-ones.