Allylic oxidation of ent-Kaurenic acid, ent-Kaurenic acid Methyl Ester and ent-Kaurenol
The allylic oxidation of ent-kaurenic acid, ent-kaurenic acid methyl ester, and ent-kaurenol with SeO2/H2O2 is presented. The reaction was run in dioxan solution at room temperature stirring for 4 hours. About 0.3 mmol of substrate was treated with 1.2 mmol of SeO2 and 4.1 mmol of H2O2. Treatment of...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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Universidad de Los Andes
2007-12-01
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| Series: | Avances en Química |
| Subjects: | |
| Online Access: | http://www.saber.ula.ve/db/ssaber/Edocs/pubelectronicas/avancesenquimica/vol2num3/articulo1.pdf |
| _version_ | 1830483045880168448 |
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| author | Rosa Aparicio Ali Bahsas Alfredo Usubillaga |
| author_facet | Rosa Aparicio Ali Bahsas Alfredo Usubillaga |
| author_sort | Rosa Aparicio |
| collection | DOAJ |
| description | The allylic oxidation of ent-kaurenic acid, ent-kaurenic acid methyl ester, and ent-kaurenol with SeO2/H2O2 is presented. The reaction was run in dioxan solution at room temperature stirring for 4 hours. About 0.3 mmol of substrate was treated with 1.2 mmol of SeO2 and 4.1 mmol of H2O2. Treatment of ent-kaurenic acid afforded 56% of ent-15α- hydroxy-kaur-16-en-19-oic acid (2a). Treatment of ent-kaurenic acid methyl ester afforded two products: ent-15α-hydroxy-kaur-16-en-19-oic acid methyl ester (2b, 34% yield) and ent-15α,16α-epoxi-17-hydroxy- kauran-19-oic acid methyl ester (3a, 59% yield). In a similar fashion treatment of ent-kaurenol rendered two products: ent-15α,17- dihydroxy-kaur-16-ene (2c, 56.7% yield) and ent-15α,16α-epoxi-17,19- dihydroxy-kaurane (3b, 34% yield). Additional experiments using twice as much or half as much H2O2 relative to the amount of SeO2 did not modify significantly the product ratio neither the yield. |
| first_indexed | 2024-12-21T17:43:59Z |
| format | Article |
| id | doaj.art-ccfa614864354417866470b5fdda6527 |
| institution | Directory Open Access Journal |
| issn | 1856-5301 |
| language | English |
| last_indexed | 2024-12-21T17:43:59Z |
| publishDate | 2007-12-01 |
| publisher | Universidad de Los Andes |
| record_format | Article |
| series | Avances en Química |
| spelling | doaj.art-ccfa614864354417866470b5fdda65272022-12-21T18:55:33ZengUniversidad de Los AndesAvances en Química1856-53012007-12-012338Allylic oxidation of ent-Kaurenic acid, ent-Kaurenic acid Methyl Ester and ent-KaurenolRosa AparicioAli BahsasAlfredo UsubillagaThe allylic oxidation of ent-kaurenic acid, ent-kaurenic acid methyl ester, and ent-kaurenol with SeO2/H2O2 is presented. The reaction was run in dioxan solution at room temperature stirring for 4 hours. About 0.3 mmol of substrate was treated with 1.2 mmol of SeO2 and 4.1 mmol of H2O2. Treatment of ent-kaurenic acid afforded 56% of ent-15α- hydroxy-kaur-16-en-19-oic acid (2a). Treatment of ent-kaurenic acid methyl ester afforded two products: ent-15α-hydroxy-kaur-16-en-19-oic acid methyl ester (2b, 34% yield) and ent-15α,16α-epoxi-17-hydroxy- kauran-19-oic acid methyl ester (3a, 59% yield). In a similar fashion treatment of ent-kaurenol rendered two products: ent-15α,17- dihydroxy-kaur-16-ene (2c, 56.7% yield) and ent-15α,16α-epoxi-17,19- dihydroxy-kaurane (3b, 34% yield). Additional experiments using twice as much or half as much H2O2 relative to the amount of SeO2 did not modify significantly the product ratio neither the yield.www.saber.ula.ve/db/ssaber/Edocs/pubelectronicas/avancesenquimica/vol2num3/articulo1.pdfAllylic oxidationselenium oxidehydrogen peroxideent-kaurenic acident-kaurenic acid methyl esterent-kaurenol |
| spellingShingle | Rosa Aparicio Ali Bahsas Alfredo Usubillaga Allylic oxidation of ent-Kaurenic acid, ent-Kaurenic acid Methyl Ester and ent-Kaurenol Avances en Química Allylic oxidation selenium oxide hydrogen peroxide ent-kaurenic acid ent-kaurenic acid methyl ester ent-kaurenol |
| title | Allylic oxidation of ent-Kaurenic acid, ent-Kaurenic acid Methyl Ester and ent-Kaurenol |
| title_full | Allylic oxidation of ent-Kaurenic acid, ent-Kaurenic acid Methyl Ester and ent-Kaurenol |
| title_fullStr | Allylic oxidation of ent-Kaurenic acid, ent-Kaurenic acid Methyl Ester and ent-Kaurenol |
| title_full_unstemmed | Allylic oxidation of ent-Kaurenic acid, ent-Kaurenic acid Methyl Ester and ent-Kaurenol |
| title_short | Allylic oxidation of ent-Kaurenic acid, ent-Kaurenic acid Methyl Ester and ent-Kaurenol |
| title_sort | allylic oxidation of ent kaurenic acid ent kaurenic acid methyl ester and ent kaurenol |
| topic | Allylic oxidation selenium oxide hydrogen peroxide ent-kaurenic acid ent-kaurenic acid methyl ester ent-kaurenol |
| url | http://www.saber.ula.ve/db/ssaber/Edocs/pubelectronicas/avancesenquimica/vol2num3/articulo1.pdf |
| work_keys_str_mv | AT rosaaparicio allylicoxidationofentkaurenicacidentkaurenicacidmethylesterandentkaurenol AT alibahsas allylicoxidationofentkaurenicacidentkaurenicacidmethylesterandentkaurenol AT alfredousubillaga allylicoxidationofentkaurenicacidentkaurenicacidmethylesterandentkaurenol |