A Concise Total Synthesis of (−)‐Berkelic Acid. (18th January 2021)

• Record Type: Journal Article
• Authors: Cheng, Hong‐Gang; Yang, Zhenjie; Chen, Ruiming; Cao, Liming; Tong, Wen‐Yan; Wei, Qiang; Wang, Qingqing; Wu, Chenggui; Qu, Shuanglin; Zhou, Qianghui
• Is Part Of: Angewandte Chemie. Volume 133:Number 10(2021)
• Page Start: 5201
• Page End: 5206
• Publication Date: 2021-01-18
• Subjects: Catellani reaction -- natural products -- reductive coupling -- spiro-compounds -- total synthesis; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202014660
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: Reported here is a concise total synthesis of (−)‐berkelic acid in eight linear steps. This synthesis features a Catellani reaction/oxa‐Michael cascade for the construction of the isochroman scaffold, a one‐pot deprotection/spiroacetalization operation for the formation of the tetracyclic core structure, and a late‐stage Ni‐catalyzed reductive coupling for the introduction of the lateral chain. Notably, four stereocenters are established from a single existing chiral center with excellent stereocontrol during the deprotection/spiroacetalization process. Stereocontrol of the intriguing deprotection/spiroacetalization process is supported by DFT calculations. Abstract : A concise total synthesis of (−)‐berkelic acid in eight linear steps was developed. This synthesis features a Catellani reaction/oxa‐Michael cascade for the construction of the isochroman scaffold, a one‐pot deprotection/spiroacetalization operation for the formation of tetracyclic core structure, and a late‐stage Ni‐catalyzed reductive coupling for the introduction of the lateral chain.