- TOTAL SYNTHESIS AND PROPERTIES OF PROSTAGLANDINS. IX. EFFECT OF THE PROTECTING GROUP OF THE OCTENOL HYDROXYL ON THE YIELD OF THE PROSTAGLANDINS AND THEIR ISOMERIC COMPOSITION
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The effect of the protecting group of 1-iodo-trans-1-octen-3-ol on the overall yield and quantitative ratio of the 15α and 15β isomers was investigated for the case of the synthesis of 11-deoxyprostaglandin E1 by the cuprate method.The positive induction effect of the protecting group of the octenol hydroxyl gives rise to an increase in the reactivity of the corresponding cuprate reagent on account of the preservation of the electron density at C1 atom of the ligand and helps to increase the yield of the prostaglandins.The protecting group sterically determines the preferred formation of one of the prostaglandin isomers.The series of diastereomeric pairs of iodooctenols were obtained for the first time in the form of their S,S-, R,R- and S,R-, R,S-acetals.The diastereomeric pairs differ significantly from each other in the reactivity of the cuprates synthesized from them.The ratio of the prostaglandin isomers formed can be predicted empirically on the basis of the difference between the chemical shifts of the vinyl protons in the PMR spectra of the protected iodooctenols.
- Korits, V. R.,Sokolov, G. P.,Freimanis, Ya. F.,Turovskii, I. V.
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p. 119 - 127
(2007/10/02)
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- Novel 2-substituted-3,4-epoxycyclopentan-1-ones, 2-substituted-3,4-epoxycyclopentan-1-ols, and various 2-substituted-cyclopentenones
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This disclosure describes novel 4-oxy-2-substituted-cyclopent-2-en-1-ones useful as intermediates for the preparation of homo and nor prostaglandins of the E2, E3 and F series.
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- Novel 11-alkoxy-9-keto (or hydroxy)-prostenoic acid derivatives and method for preparing same
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This disclosure describes certain 11-alkoxy-9-keto- (or hydroxy)-prostenoic acid derivatives useful as anti-microbial agents, hypotensive agents, anti-ulcer agents, or as intermediates.
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- Hydro substituted prostanoic acids and esters
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This disclosure describes certain 11-hydroxy and 11-deoxy-9-keto (or hydroxy)prostanoic acid derivatives useful as bronchodilators, anti-ulcer agents, or as intermediates.
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- Novel 11-hydroxy-9-keto-5,6-cis-13,14-cis-prostadienoic acid derivatives
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This disclosure describes certain 11-hydroxy and 11-deoxy-9-keto(or hydroxy)-prostanoic acid derivatives useful as bronchodilators, hypotensive agents, anti-ulcer agents, or as intermediates.
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- Lithium 3-triphenylmethoxy-1-trans-alkenyl-dialkyl alanates
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This disclosure describes 3-triphenylmethoxy-1-alkynes, 3-triphenylmethoxy-1-trans-alkenyl-dialkyl-alanes, and lithium 3-triphenylmethoxy-1-trans-alkenyl-dialkyl alanates useful as intermediates for the preparation of certain 11-hydroxy- and 11-deoxy-9-keto(or hydroxy)-prostanoic acid derivatives which possess bronchodilator, hypotensive, and anti-ulcer activity.
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- 2-Substituted-3,4-epoxycyclopentan-1-ones, and 2-substituted-3,4-epoxycyclopentan-1-ols
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This disclosure describes 2-substituted-3,4-epoxy-cyclopentan-1-ones, 2-substituted-3,4-epoxycyclopentan-1-ols, and various 2-substituted-cyclopentenones useful as intermediates for the preparation of certain 11-hydroxy- and 11-deoxy-9-keto(or hydroxy)-prostanoic acid derivatives which possess bronchodilator, hypotensive, and anti-ulcer activity.
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