Transformations of 3,7-interphenylene 11-deoxyprostanoid formyl precursors in the acidic medium

Abstract

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.