The syntheses of the marine metabolites 3-bromoverongiaquinol and 5-monobromocavernicolin
An efficient synthesis of the marine metabolite 3-bromoverongiaquinol (1) and the first total synthesis of 5-monobromocavernicolin (2), both isolated from the marine sponge Aplysina cavernicola, have been described based on the 1,2 addition of the lithium enolate of N,O-bistrimethylsilylacetamide (B...
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| Format: | Article |
| Language: | English |
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Sociedade Brasileira de Química
2010-01-01
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| Series: | Química Nova |
| Subjects: | |
| Online Access: | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422010001000007 |
| _version_ | 1818155995849818112 |
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| author | Luiz Antonio Fonseca de Godoy Ronaldo Aloise Pilli |
| author_facet | Luiz Antonio Fonseca de Godoy Ronaldo Aloise Pilli |
| author_sort | Luiz Antonio Fonseca de Godoy |
| collection | DOAJ |
| description | An efficient synthesis of the marine metabolite 3-bromoverongiaquinol (1) and the first total synthesis of 5-monobromocavernicolin (2), both isolated from the marine sponge Aplysina cavernicola, have been described based on the 1,2 addition of the lithium enolate of N,O-bistrimethylsilylacetamide (BSA, 4) to 1,4-benzoquinone (3). Bromination and purification of the crude product on silica gel chromatography provided 3-bromoverongiaquinol (1) in 50% overall yield. Under alkaline conditions, the crude product of the bromination reaction was converted to 5-monobromocavernicolin (2) in 20% yield which was also obtained in 13% yield (25% yield based on recovered starting material) from 3-bromoverongiaquinol (1). |
| first_indexed | 2024-12-11T14:51:16Z |
| format | Article |
| id | doaj.art-a9adb1bd8de14d20a47320b36f1535d1 |
| institution | Directory Open Access Journal |
| issn | 0100-4042 1678-7064 |
| language | English |
| last_indexed | 2024-12-11T14:51:16Z |
| publishDate | 2010-01-01 |
| publisher | Sociedade Brasileira de Química |
| record_format | Article |
| series | Química Nova |
| spelling | doaj.art-a9adb1bd8de14d20a47320b36f1535d12022-12-22T01:01:27ZengSociedade Brasileira de QuímicaQuímica Nova0100-40421678-70642010-01-0133102042204510.1590/S0100-40422010001000007The syntheses of the marine metabolites 3-bromoverongiaquinol and 5-monobromocavernicolinLuiz Antonio Fonseca de GodoyRonaldo Aloise PilliAn efficient synthesis of the marine metabolite 3-bromoverongiaquinol (1) and the first total synthesis of 5-monobromocavernicolin (2), both isolated from the marine sponge Aplysina cavernicola, have been described based on the 1,2 addition of the lithium enolate of N,O-bistrimethylsilylacetamide (BSA, 4) to 1,4-benzoquinone (3). Bromination and purification of the crude product on silica gel chromatography provided 3-bromoverongiaquinol (1) in 50% overall yield. Under alkaline conditions, the crude product of the bromination reaction was converted to 5-monobromocavernicolin (2) in 20% yield which was also obtained in 13% yield (25% yield based on recovered starting material) from 3-bromoverongiaquinol (1).http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422010001000007Aplysina cavernicola3-bromoverongiaquinol and 5-monobromocavernicolinsynthesis |
| spellingShingle | Luiz Antonio Fonseca de Godoy Ronaldo Aloise Pilli The syntheses of the marine metabolites 3-bromoverongiaquinol and 5-monobromocavernicolin Química Nova Aplysina cavernicola 3-bromoverongiaquinol and 5-monobromocavernicolin synthesis |
| title | The syntheses of the marine metabolites 3-bromoverongiaquinol and 5-monobromocavernicolin |
| title_full | The syntheses of the marine metabolites 3-bromoverongiaquinol and 5-monobromocavernicolin |
| title_fullStr | The syntheses of the marine metabolites 3-bromoverongiaquinol and 5-monobromocavernicolin |
| title_full_unstemmed | The syntheses of the marine metabolites 3-bromoverongiaquinol and 5-monobromocavernicolin |
| title_short | The syntheses of the marine metabolites 3-bromoverongiaquinol and 5-monobromocavernicolin |
| title_sort | syntheses of the marine metabolites 3 bromoverongiaquinol and 5 monobromocavernicolin |
| topic | Aplysina cavernicola 3-bromoverongiaquinol and 5-monobromocavernicolin synthesis |
| url | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422010001000007 |
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