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Total Syntheses of Bisdehydroneostemoninine and Bisdehydrostemoninine by Catalytic Carbonylative Spirolactonization
Author(s) -
Ma Kaiqing,
Yin Xianglin,
Dai Mingji
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201809114
Subject(s) - moiety , chemistry , tandem , carbonylation , tricyclic , catalysis , total synthesis , friedel–crafts reaction , stereochemistry , combinatorial chemistry , organic chemistry , carbon monoxide , materials science , composite material
The first total syntheses of the stemona alkaloids bisdehydroneostemoninine and bisdehydrostemoninine in racemic forms have been achieved. The synthetic strategy features a novel palladium‐catalyzed carbonylative spirolactonization of a hydroxycyclopropanol to rapidly construct the oxaspirolactone moiety. It also features a Lewis acid promoted tandem Friedel–Crafts cyclization and lactonization to form the 5‐7‐5 tricyclic core of the target stemona alkaloids.