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This is a Experimental Study study.

October 2, 2025

Total Syntheses of Giraldine I and Heterophyllisine

CLChuang LiUniversity of Electronic Science and Technology of China FLFei LüXinjiang Entry-Exit Inspection and Quarantine Bureau NWNingwei WangSichuan University

Puntos clave

Total syntheses of giraldine I and heterophyllisine were successfully achieved using novel chemical strategies.
Key techniques included allene hydrocyanation and skeletal editing to construct the tetracyclic scaffold.
The research utilized bioinspired oxidations to accurately form the lactone-type alkaloid from aconitines.
Innovative methods like Claisen rearrangement and ring-closing metathesis played a crucial role in synthesis.

Resumen

Aconitine and related norditerpenoid alkaloids are chemically and biologically significant natural products that represent a formidable synthetic challenge. Here, we report the first total syntheses of aconitine-type alkaloid giraldine I and lactone-type alkaloid heterophyllisine. Key strategies include (1) early stage installation of the C4 all-carbon quaternary stereocenter and nitrogen atom via allene hydrocyanation, (2) skeletal editing through hydrodealkenylative fragmentation/Mannich cyclization to build the A/B/E/F tetracyclic scaffold, (3) a Claisen rearrangement/ring-closing metathesis (RCM) sequence followed by transannular pinacol coupling to form the characteristic C/D rings of aconitines, and (4) a bioinspired and regioselective Baeyer-Villiger oxidation to access the lactone-type alkaloid.

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