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Total Syntheses of the Reported Structures of Curcusones I and J through Tandem Gold Catalysis
Author(s) -
Li Yong,
Dai Mingji
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201706845
Subject(s) - allene , tandem , furan , cycloaddition , chemistry , ring (chemistry) , stereoselectivity , catalysis , stereochemistry , diterpene , combinatorial chemistry , organic chemistry , materials science , composite material
Total syntheses of the reported structures of the rhamnofolane diterpene natural products curcusones I and J in racemic form were achieved. The synthetic strategy features a novel tandem gold‐catalyzed furan formation and furan–allene [4+3] cycloaddition to build the 5,7‐fused ring system with an oxa‐bridge in one step, and a stereoselective exo ‐Diels–Alder reaction to form the 6‐membered ring. The newly developed tandem gold catalysis is quite general and can be scaled up. Our syntheses suggest that structural revisions of curcusones I and J are needed.