Studies towards Bioinspired Synthesis of Hetidine‐Type C20‐Diterpenoid Alkaloids. Issue 6 (28th April 2017)

• Record Type: Journal Article
• Authors: Zhu, Min; Li, Xiaohuan; Song, Xue; Wang, Zhixiu; Liu, Xiaoyu; Song, Hao; Zhang, Dan; Wang, Fengpeng; Qin, Yong
• Is Part Of: Chinese journal of chemistry. Volume 35:Issue 6(2017)
• Page Start: 991
• Page End: 1000
• Publication Date: 2017-04-28
• Subjects: alkaloids -- bioinspired synthesis -- C—H oxidation -- cyclization -- terpenoids; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/cjoc.201600853
• Languages: English
• ISSNs: 1001-604X

Abstract

Abstract: Details of a biogenetically inspired strategy that led to the synthesis of the hetidine‐type C20 ‐diterpenoid alkaloid skeleton are reported in this paper. Key steps of our synthesis include a C—H oxidation to convert the atisine‐type core to the ajaconine skeleton, as well as an aza ‐Prins cyclization that establishes the hetidine alkaloid skeleton. An unexpected heptacyclic framework bearing a unique tricyclo[3.3.1.0 2, 7 ]nonane moiety has been obtained during our studies, which may represent a new type of C20 ‐diterpenoid alkaloids yet to be discovered. Abstract : Details of our synthetic efforts towards the hetidine‐type C20 ‐diterpenoid alkaloid skeleton that rely on the biogenetically related atisine and ajaconine intermediates are reported. Key steps of our synthesis include a C‐H oxidation and an aza ‐Prins cyclization.