The Total Synthesis of Diquinane‐Containing Natural Products

• Published in: Chemistry : a European journal Vol. 27; no. 15; pp. 4839 - 4858
• Main Authors: Li, Huilin, Zhang, Jing, She, Xuegong
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 12.03.2021
• Subjects: bicyclo[3.3.0]octane; Chemistry; diquinane; Natural products; Synthesis; synthetic strategy; Terpenes; total synthesis; natural products; synthetic strategy; diquinane; total synthesis; bicyclo[3.3.0]octane
• ISSN: 0947-6539; 1521-3765; 1521-3765
• DOI: 10.1002/chem.202003741

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.