Vicinally substituted cyclopentenes and cyclopentenones from (±)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one

Verfasser / Beitragende:
[V. Akhmet'yanova, N. Ivanova, Z. Valiullina, M. Miftakhov]
Ort, Verlag, Jahr:
2015
Enthalten in:
Russian Journal of Organic Chemistry, 51/3(2015-03-01), 319-324
Format:
Artikel (online)
ID: 605529779
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024 7 0 |a 10.1134/S1070428015030057  |2 doi 
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245 0 0 |a Vicinally substituted cyclopentenes and cyclopentenones from (±)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one  |h [Elektronische Daten]  |c [V. Akhmet'yanova, N. Ivanova, Z. Valiullina, M. Miftakhov] 
520 3 |a Solvolysis of (±)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one in a mixture of tert-butyl alcohol with water and triethylamine, followed by successive treatment with K2CO3, NaBH4, and CH2N2, gave methyl 2-(hydroxymethyl)cyclopent-2-ene-1-carboxylate which was subjected to hydride reduction, epoxidation, trichloroacetimidation, and acetylation. Allylic oxidation of methyl 2-(acetoxymethyl)cyclopent-2-ene-1-carboxylate with the chromium(VI) oxide-3,5-dimethylpyrazole complex afforded methyl 2-(acetoxymethyl)-4-oxocyclopent-2-ene-1-carboxylate, and methyl (1R*,2R*,5R*)-1-(hydroxymethyl)-6-oxabicyclo[3.1.0]-hexane-2-carboxylate was converted into a building block for the synthesis of deoxyentecavir and sarcomycine methyl ester. 
540 |a Pleiades Publishing, Ltd., 2015 
700 1 |a Akhmet'yanova  |D V.  |u Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, 450054, Ufa, Bashkortostan, Russia  |4 aut 
700 1 |a Ivanova  |D N.  |u Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, 450054, Ufa, Bashkortostan, Russia  |4 aut 
700 1 |a Valiullina  |D Z.  |u Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, 450054, Ufa, Bashkortostan, Russia  |4 aut 
700 1 |a Miftakhov  |D M.  |u Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, 450054, Ufa, Bashkortostan, Russia  |4 aut 
773 0 |t Russian Journal of Organic Chemistry  |d Pleiades Publishing  |g 51/3(2015-03-01), 319-324  |x 1070-4280  |q 51:3<319  |1 2015  |2 51  |o 11178 
856 4 0 |u https://doi.org/10.1134/S1070428015030057  |q text/html  |z Onlinezugriff via DOI 
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908 |D 1  |a research-article  |2 jats 
949 |B NATIONALLICENCE  |F NATIONALLICENCE  |b NL-springer 
950 |B NATIONALLICENCE  |P 856  |E 40  |u https://doi.org/10.1134/S1070428015030057  |q text/html  |z Onlinezugriff via DOI 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Akhmet'yanova  |D V.  |u Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, 450054, Ufa, Bashkortostan, Russia  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Ivanova  |D N.  |u Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, 450054, Ufa, Bashkortostan, Russia  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Valiullina  |D Z.  |u Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, 450054, Ufa, Bashkortostan, Russia  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Miftakhov  |D M.  |u Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, 450054, Ufa, Bashkortostan, Russia  |4 aut 
950 |B NATIONALLICENCE  |P 773  |E 0-  |t Russian Journal of Organic Chemistry  |d Pleiades Publishing  |g 51/3(2015-03-01), 319-324  |x 1070-4280  |q 51:3<319  |1 2015  |2 51  |o 11178