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Studies towards Bioinspired Synthesis of Hetidine‐Type C 20 ‐Diterpenoid Alkaloids
Author(s) -
Zhu Min,
Li Xiaohuan,
Song Xue,
Wang Zhixiu,
Liu Xiaoyu,
Song Hao,
Zhang Dan,
Wang Fengpeng,
Qin Yong
Publication year - 2017
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201600853
Subject(s) - chemistry , moiety , nonane , terpenoid , stereochemistry , skeleton (computer programming) , alkaloid , carbon skeleton , ring (chemistry) , organic chemistry , computer science , programming language
Details of a biogenetically inspired strategy that led to the synthesis of the hetidine‐type C 20 ‐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 C 20 ‐diterpenoid alkaloids yet to be discovered.