Diels-Alder/Oxidative Aromatization Approach towards the All-Carbon DEF Tricyclic Skeleton of Daphenylline
Daphenylline is a recently isolated Daphniphyllum alkaloid with an unprecedented novel hexacyclic scaffold. In this study, the synthesis of the fused all‐carbon DEF tricyclic skeleton of daphenylline has been accomplished. Key steps of the reported sequence involve Evans asymmetric allylation, aldol...
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| Published in | Chemistry, an Asian journal Vol. 9; no. 5; pp. 1274 - 1277 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
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Weinheim
WILEY-VCH Verlag
01.05.2014
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| Abstract | Daphenylline is a recently isolated Daphniphyllum alkaloid with an unprecedented novel hexacyclic scaffold. In this study, the synthesis of the fused all‐carbon DEF tricyclic skeleton of daphenylline has been accomplished. Key steps of the reported sequence involve Evans asymmetric allylation, aldol condensation, Diels–Alder reaction, and oxidative aromatization reactions. The developed strategy might lead to the total synthesis of daphenylline.
DEF‐initely maybe: Synthesis of the fused all‐carbon DEF tricyclic skeleton of daphenylline, a structurally novel Daphniphyllum alkaloid, has been accomplished based on a Diels–Alder/oxidative aromatization strategy. The finished approach, in combination with our previous research for the construction of the ABC ring system, may lead to the asymmetric total synthesis of daphenylline. |
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| AbstractList | Daphenylline is a recently isolated Daphniphyllum alkaloid with an unprecedented novel hexacyclic scaffold. In this study, the synthesis of the fused all-carbon DEF tricyclic skeleton of daphenylline has been accomplished. Key steps of the reported sequence involve Evans asymmetric allylation, aldol condensation, Diels-Alder reaction, and oxidative aromatization reactions. The developed strategy might lead to the total synthesis of daphenylline. Daphenylline is a recently isolated Daphniphyllum alkaloid with an unprecedented novel hexacyclic scaffold. In this study, the synthesis of the fused all-carbon DEF tricyclic skeleton of daphenylline has been accomplished. Key steps of the reported sequence involve Evans asymmetric allylation, aldol condensation, Diels-Alder reaction, and oxidative aromatization reactions. The developed strategy might lead to the total synthesis of daphenylline. [PUBLICATION ABSTRACT] Daphenylline is a recently isolated Daphniphyllum alkaloid with an unprecedented novel hexacyclic scaffold. In this study, the synthesis of the fused all-carbon DEF tricyclic skeleton of daphenylline has been accomplished. Key steps of the reported sequence involve Evans asymmetric allylation, aldol condensation, Diels-Alder reaction, and oxidative aromatization reactions. The developed strategy might lead to the total synthesis of daphenylline.Daphenylline is a recently isolated Daphniphyllum alkaloid with an unprecedented novel hexacyclic scaffold. In this study, the synthesis of the fused all-carbon DEF tricyclic skeleton of daphenylline has been accomplished. Key steps of the reported sequence involve Evans asymmetric allylation, aldol condensation, Diels-Alder reaction, and oxidative aromatization reactions. The developed strategy might lead to the total synthesis of daphenylline. Daphenylline is a recently isolated Daphniphyllum alkaloid with an unprecedented novel hexacyclic scaffold. In this study, the synthesis of the fused all‐carbon DEF tricyclic skeleton of daphenylline has been accomplished. Key steps of the reported sequence involve Evans asymmetric allylation, aldol condensation, Diels–Alder reaction, and oxidative aromatization reactions. The developed strategy might lead to the total synthesis of daphenylline. DEF‐initely maybe: Synthesis of the fused all‐carbon DEF tricyclic skeleton of daphenylline, a structurally novel Daphniphyllum alkaloid, has been accomplished based on a Diels–Alder/oxidative aromatization strategy. The finished approach, in combination with our previous research for the construction of the ABC ring system, may lead to the asymmetric total synthesis of daphenylline. |
| Author | Xie, Xingang Zhao, Changgui Yuan, Ziyun She, Xuegong Qiu, Yangcheng Li, Huilin |
| Author_xml | – sequence: 1 givenname: Huilin surname: Li fullname: Li, Huilin organization: State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000 (P. R. China), Fax:(+86) 931-8912582 – sequence: 2 givenname: Yangcheng surname: Qiu fullname: Qiu, Yangcheng organization: State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000 (P. R. China), Fax:(+86) 931-8912582 – sequence: 3 givenname: Changgui surname: Zhao fullname: Zhao, Changgui organization: State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000 (P. R. China), Fax:(+86) 931-8912582 – sequence: 4 givenname: Ziyun surname: Yuan fullname: Yuan, Ziyun organization: State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000 (P. R. China), Fax:(+86) 931-8912582 – sequence: 5 givenname: Xingang surname: Xie fullname: Xie, Xingang organization: State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000 (P. R. China), Fax:(+86) 931-8912582 – sequence: 6 givenname: Xuegong surname: She fullname: She, Xuegong email: shexg@lzu.edu.cn organization: State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000 (P. R. China), Fax:(+86) 931-8912582 |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/24591463$$D View this record in MEDLINE/PubMed |
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| Keywords | natural products aromatization Diels-Alder daphenylline alkaloids |
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| Snippet | Daphenylline is a recently isolated Daphniphyllum alkaloid with an unprecedented novel hexacyclic scaffold. In this study, the synthesis of the fused... |
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| SubjectTerms | alkaloids Alkaloids - chemical synthesis Alkaloids - chemistry aromatization Chemistry Cycloaddition Reaction daphenylline Diels-Alder Molecular Structure natural products Oxidation-Reduction |
| Title | Diels-Alder/Oxidative Aromatization Approach towards the All-Carbon DEF Tricyclic Skeleton of Daphenylline |
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