59829-44-6Relevant academic research and scientific papers
Haloiminolactonization of cyclopentene α,α-dichlorocarboxamides. Tandem rearrangement of iminolactones in epoxylactones
Valiullina,Akhmet'Yanova,Ivanova,Erastov,Meshcheryakova,Miftakhov
, p. 1524 - 1531 (2015/12/30)
Electrophilic cyclization initiated by NBS and I2 of 2,2-dichloro-2-[(1R,5S)- and 2,2-dichloro-2-[(1S,5R)-5-hydroxy-2-cyclopent-2-en-1-yl]-N-[(1R)-1-phenylethyl]acetamides was investigated. Stable under conditions of chromatography on SiO2 bicyclic iminoesters, (2Z,3aS,4S,6S,6aS)-6-bromo-3,3-dichloro- and (2Z,3aS,4S,6S,6aS)-3,3-dichloro-6-iodo-2-{[(1R)-1-phenylethyl]imino}hexahydro-2H-cyclopenta[b]furan-4-ols were isolated and characterized, and a possible version was suggested of their step-by-step recyclization transformations. The halocyclization of carboxamides in water-organic mixtures afforded bicyclic epoxylactones (1aR,2aS,5aS,5bS)- and (1aS,2aR,5aR,5bR)-5,5-dichlorohexahydro-4H-oxireno[3,4]cyclopenta-[1,2-b]furan-4-ones, whose reductive dechlorination proceeded stepwise with successive removal of Cl atoms and led to the formation of (1aR,2aS,5aS,5bS)- and (1aS,2aR,5aR,5bR)-hexahydro-4H-oxireno[3,4]cyclopenta-[1,2-b]furan-4-ones.
Tandem transformations of cyclopentene α,α-dichlorocarboxamides into epoxy lactones induced by a γ-hydroxyl group; A short synthesis of the Corey epoxy lactone and its enantiomer
Valiullina, Zuleykha R.,Akhmetyanova, Vera A.,Ivanova, Nadezhda A.,Miftakhov, Mansur S.
, p. 6904 - 6907 (2015/11/27)
The stable iminolactone 6 was obtained by NBS induced bromocyclization of carboxamide 4. Under treatment of 6 with DBU a tandem recyclization transformation occurred resulting in the formation of epoxyiminolactone 7. Bromo(iodo)cyclization of 4 in aqueous organic medium followed by treatment with base gave epoxylactone 9. Under the optimized conditions, Corey epoxylactone 1 and its enantiomer ent-1 were obtained from diastereomeric carboxamides 4 and 5 in an overall yield of 40%.
Functionalised Carbocycles from Carbohydrates. Part 3. The Synthesis of the Epoxy Lactone Prostaglandin Intermediate via an Isoxazolidine Derivative. X-Ray Crystal Structure of (1R,5R)-6-exo,7-endo-Dibenzoyloxy-8-exo-iodo-3-oxo-2-oxabicyclooctane
Ferrier, Robert J.,Prasit, Petpiboon,Gainsford, Graeme J.
, p. 1629 - 1634 (2007/10/02)
The bicyclic isoxazolidine 6,7-dibenzoyloxy-N-methyl-8-tosyloxy-3-oxa-2-azabicyclooctane (1), which is easily obtained from a readily available D-glucose derivative, has been converted into the epoxy lactone 8-oxo-3,7-dioxatricyclo2,4>nonane (13), via a series of cyclopentane derivatives, in ten steps.Since the product (13) can be used to prepare prostaglandins this sequence represents a new route to these compounds in their enantiomerically pure natural form.
NEW METHODS AND REAGENTS IN ORGANIC SYNTHESIS. 15. EPOXIDATION OF OLEFINS WITH DIETHYL PHOSPHOROCYANIDATE (DEPC) AND HYDROGEN PEROXIDE
Mizuno, Akira,Hamada, Yasumasa,Shioiri, Takayuki
, p. 1774 - 1776 (2007/10/02)
A mixture of diethyl phosphorocyanidate (DEPC) and hydrogen peroxide in the presence of 2-hydroxypyridine or 1,2,4-triazole functions as an epoxidizing agent for olefins.Keywords: diethyl phosphorocyanidate; hydrogen peroxide; epoxidation; 2-hydroxypyridine; 1,2,4-triazole; peroxyphosphoric acid
A General Route to Optically Pure Prostaglandins from a D-Glucose Derivative
Ferrier, Robert J.,Prasit, Petpiboon
, p. 983 - 985 (2007/10/02)
The epoxy-lactone (14), which is a key intermediate in one synthetic route to prostaglandins, has been prepared from a readily available D-glucose derivative.
