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.
Highlights
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 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
P. Bimatoprost: a review of its use in open-angle glaucoma and ocular hypertension / M
Summary
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. В [9] нами описана схема синтеза циклопентеноновых синтонов для 11-дезокси-3-окса-3,7-интер-м-фениленовых аналогов простагландинов. В настоящей работе описаны обнаруженные нами особенности поведения образующихся при кислотном гидролизе ацеталей (7–9) 2-(арилалкил)-3-оксоциклопентан-1-карбальдегидов (10–12) в кислой среде.
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