The Total Synthesis of Diquinane‐Containing Natural Products
Diquinane or bicyclo[3.3.0]octane is a conspicuous structural unit existing in the carbo‐frameworks of a wide range of natural products such as alkaloids and terpenoids. These diquinane‐containing molecules not merely exhibit intriguing architectures, but also showcase a broad spectrum of significan...
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Published in | Chemistry : a European journal Vol. 27; no. 15; pp. 4839 - 4858 |
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Format | Journal Article |
Language | English |
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12.03.2021
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Abstract | Diquinane or bicyclo[3.3.0]octane is a conspicuous structural unit existing in the carbo‐frameworks of a wide range of natural products such as alkaloids and terpenoids. These diquinane‐containing molecules not merely exhibit intriguing architectures, but also showcase a broad spectrum of significant bioactivities, which draw widespread attention from the global synthetic community. During the past decade, with an aim to accomplish the total syntheses of such specified cornucopias of natural products, a variety of elegant strategies for construction of the diquinane ring system have been disclosed. In this Minireview, the achievements on this subject in the timeline from 2010 to June 2020 are demonstrated and it is discussed how the diquinane unit is strategically forged in the context of the specific target structure. In addition, impacts of the selected works to the field of natural product total synthesis is highlighted and the particular outlook of diquinane‐containing natural product synthesis is provided.
Natural products bearing a diquinane motif generally exhibit complex intriguing architectures as well as significant bioactivities. Aiming to their total synthesis, a variety of methods have been developed to construct this prevalent substructure in recent years. In this Minireview, the methods for construction of diquinane motif reported in the past decade (2010–2020) are summarized and discussed in the context of natural product total synthesis. |
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AbstractList | Diquinane or bicyclo[3.3.0]octane is a conspicuous structural unit existing in the carbo‐frameworks of a wide range of natural products such as alkaloids and terpenoids. These diquinane‐containing molecules not merely exhibit intriguing architectures, but also showcase a broad spectrum of significant bioactivities, which draw widespread attention from the global synthetic community. During the past decade, with an aim to accomplish the total syntheses of such specified cornucopias of natural products, a variety of elegant strategies for construction of the diquinane ring system have been disclosed. In this Minireview, the achievements on this subject in the timeline from 2010 to June 2020 are demonstrated and it is discussed how the diquinane unit is strategically forged in the context of the specific target structure. In addition, impacts of the selected works to the field of natural product total synthesis is highlighted and the particular outlook of diquinane‐containing natural product synthesis is provided. Diquinane or bicyclo[3.3.0]octane is a conspicuous structural unit existing in the carbo-frameworks of a wide range of natural products such as alkaloids and terpenoids. These diquinane-containing molecules not merely exhibit intriguing architectures, but also showcase a broad spectrum of significant bioactivities, which draw widespread attention from the global synthetic community. During the past decade, with an aim to accomplish the total syntheses of such specified cornucopias of natural products, a variety of elegant strategies for construction of the diquinane ring system have been disclosed. In this Minireview, the achievements on this subject in the timeline from 2010 to June 2020 are demonstrated and it is discussed how the diquinane unit is strategically forged in the context of the specific target structure. In addition, impacts of the selected works to the field of natural product total synthesis is highlighted and the particular outlook of diquinane-containing natural product synthesis is provided.Diquinane or bicyclo[3.3.0]octane is a conspicuous structural unit existing in the carbo-frameworks of a wide range of natural products such as alkaloids and terpenoids. These diquinane-containing molecules not merely exhibit intriguing architectures, but also showcase a broad spectrum of significant bioactivities, which draw widespread attention from the global synthetic community. During the past decade, with an aim to accomplish the total syntheses of such specified cornucopias of natural products, a variety of elegant strategies for construction of the diquinane ring system have been disclosed. In this Minireview, the achievements on this subject in the timeline from 2010 to June 2020 are demonstrated and it is discussed how the diquinane unit is strategically forged in the context of the specific target structure. In addition, impacts of the selected works to the field of natural product total synthesis is highlighted and the particular outlook of diquinane-containing natural product synthesis is provided. Diquinane or bicyclo[3.3.0]octane is a conspicuous structural unit existing in the carbo‐frameworks of a wide range of natural products such as alkaloids and terpenoids. These diquinane‐containing molecules not merely exhibit intriguing architectures, but also showcase a broad spectrum of significant bioactivities, which draw widespread attention from the global synthetic community. During the past decade, with an aim to accomplish the total syntheses of such specified cornucopias of natural products, a variety of elegant strategies for construction of the diquinane ring system have been disclosed. In this Minireview, the achievements on this subject in the timeline from 2010 to June 2020 are demonstrated and it is discussed how the diquinane unit is strategically forged in the context of the specific target structure. In addition, impacts of the selected works to the field of natural product total synthesis is highlighted and the particular outlook of diquinane‐containing natural product synthesis is provided. Natural products bearing a diquinane motif generally exhibit complex intriguing architectures as well as significant bioactivities. Aiming to their total synthesis, a variety of methods have been developed to construct this prevalent substructure in recent years. In this Minireview, the methods for construction of diquinane motif reported in the past decade (2010–2020) are summarized and discussed in the context of natural product total synthesis. |
Author | Zhang, Jing She, Xuegong Li, Huilin |
Author_xml | – sequence: 1 givenname: Huilin orcidid: 0000-0001-8088-6718 surname: Li fullname: Li, Huilin email: lihuilin@lzu.edu.cn organization: Lanzhou University – sequence: 2 givenname: Jing orcidid: 0000-0003-4454-0829 surname: Zhang fullname: Zhang, Jing organization: Lanzhou University – sequence: 3 givenname: Xuegong orcidid: 0000-0002-3002-2433 surname: She fullname: She, Xuegong email: shexg@lzu.edu.cn organization: Lanzhou University |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/32955141$$D View this record in MEDLINE/PubMed |
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CitedBy_id | crossref_primary_10_1016_j_xcrp_2024_101855 crossref_primary_10_1021_jacs_3c03178 crossref_primary_10_1021_jacs_5c00319 crossref_primary_10_1002_adsc_202301090 crossref_primary_10_1039_D2QO01410F crossref_primary_10_1021_acs_orglett_2c01352 crossref_primary_10_1002_adsc_202401015 crossref_primary_10_1021_jacs_4c09555 crossref_primary_10_1021_jacs_3c07044 crossref_primary_10_1021_jacs_1c13370 crossref_primary_10_1039_D4OB00984C crossref_primary_10_1021_acs_orglett_3c02956 crossref_primary_10_1002_anie_202413275 crossref_primary_10_1021_acs_orglett_4c03089 crossref_primary_10_1002_ange_202413275 |
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Keywords | natural products synthetic strategy diquinane total synthesis bicyclo[3.3.0]octane |
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Snippet | Diquinane or bicyclo[3.3.0]octane is a conspicuous structural unit existing in the carbo‐frameworks of a wide range of natural products such as alkaloids and... Diquinane or bicyclo[3.3.0]octane is a conspicuous structural unit existing in the carbo-frameworks of a wide range of natural products such as alkaloids and... |
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SubjectTerms | bicyclo[3.3.0]octane Chemistry diquinane Natural products Synthesis synthetic strategy Terpenes total synthesis |
Title | The Total Synthesis of Diquinane‐Containing Natural Products |
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