Studies towards Bioinspired Synthesis of Hetidine‐Type C20‐Diterpenoid Alkaloids

Chinese Journal of Chemistry
2017.0

Abstract

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.

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