Enantioselective total synthesis of cytotoxic taiwaniaquinones A and F
The first synthesis of cytotoxic (-)-taiwaniaquinone A and (-)-taiwaniaquinone F has been achieved through the intramolecular aldol condensation of a ketoaldehyde and the oxidative cleavage of an isopropylidene ketal.
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| Published in | Chemical communications (Cambridge, England) Vol. 46; no. 48; pp. 9244 - 9246 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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CAMBRIDGE
Royal Soc Chemistry
28.12.2010
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| Subjects | |
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| Abstract | The first synthesis of cytotoxic (-)-taiwaniaquinone A and (-)-taiwaniaquinone F has been achieved through the intramolecular aldol condensation of a ketoaldehyde and the oxidative cleavage of an isopropylidene ketal. |
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| AbstractList | The first synthesis of cytotoxic (-)-taiwaniaquinone A and (-)-taiwaniaquinone F has been achieved through the intramolecular aldol condensation of a ketoaldehyde and the oxidative cleavage of an isopropylidene ketal. |
| Author | Chahboun, Rachid Alvarez-Manzaneda, Ramon Alvarez-Manzaneda, Enrique Alvarez, Esteban Tapia, Ruben |
| Author_xml | – sequence: 1 givenname: Enrique surname: Alvarez-Manzaneda fullname: Alvarez-Manzaneda, Enrique email: eamr@ugr.es organization: Univ Granada, Fac Ciencias, Dept Quim Organ, Inst Biotecnol, E-18071 Granada, Spain – sequence: 2 givenname: Rachid surname: Chahboun fullname: Chahboun, Rachid organization: Univ Granada, Fac Ciencias, Dept Quim Organ, Inst Biotecnol, E-18071 Granada, Spain – sequence: 3 givenname: Esteban surname: Alvarez fullname: Alvarez, Esteban organization: Univ Granada, Fac Ciencias, Dept Quim Organ, Inst Biotecnol, E-18071 Granada, Spain – sequence: 4 givenname: Ruben surname: Tapia fullname: Tapia, Ruben organization: Univ Granada, Fac Ciencias, Dept Quim Organ, Inst Biotecnol, E-18071 Granada, Spain – sequence: 5 givenname: Ramon surname: Alvarez-Manzaneda fullname: Alvarez-Manzaneda, Ramon organization: Univ Almeria, Fac Ciencias, Dept Quim Organ, Almeria 04120, Spain |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/21042617$$D View this record in MEDLINE/PubMed |
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| Cites_doi | 10.1021/jo900153y 10.1021/ja054447p 10.1016/j.bmc.2007.01.031 10.1021/ja061853f 10.1021/ol800513v 10.1016/j.tetlet.2008.01.084 10.1021/ja003541x 10.1021/ja062505g 10.1021/np9004695 10.1039/b916209g 10.1021/jo052454q 10.1016/j.tetasy.2007.11.024 10.1021/ol035506b 10.1055/s-2005-837754 10.1039/b300377a 10.1021/jo052589w 10.1016/0040-4039(94)85084-4 10.1039/B816812A 10.1016/0031-9422(96)00198-7 10.1016/0040-4020(75)87048-7 10.1016/S0031-9422(98)00471-3 10.1039/c39720000886 10.1055/s-2002-33787 10.1016/S0040-4039(99)01191-0 10.1016/0031-9422(95)00358-E 10.1016/0040-4020(75)87049-9 10.1016/S0968-0896(01)00099-2 10.1248/cpb.51.1420 10.1080/00304948909356425 10.1016/0040-4020(89)80132-2 10.1039/c39750000282 10.1021/jo00211a030 |
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| Issue | 48 |
| Keywords | DITERPENES ACID BARK EFFICIENT ROUTE (+/-)-DICHROANONE CRYPTOMERIOIDES AROMATASE THUJA-STANDISHII (+/-)-TAIWANIAQUINOL-B SKELETON |
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| Snippet | The first synthesis of cytotoxic (-)-taiwaniaquinone A and (-)-taiwaniaquinone F has been achieved through the intramolecular aldol condensation of a... |
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| SubjectTerms | Aldehydes - chemistry Chemistry Chemistry, Multidisciplinary Cytotoxins - chemical synthesis Ketones - chemistry Physical Sciences Pinus - chemistry Quinones - chemical synthesis Science & Technology Stereoisomerism Taiwan Terpenes |
| Title | Enantioselective total synthesis of cytotoxic taiwaniaquinones A and F |
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