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Rapid Access to the Tricyclic Core of Calyciphylline A ‐Type Alkaloids Through Allyl Cyanate‐to‐Isocyanate Rearrangement
Author(s) -
Baidilov Daler,
Miskey Scott,
Hudlicky Tomas
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901549
Subject(s) - chemistry , tricyclic , intramolecular force , isocyanate , transposition (logic) , combinatorial chemistry , cyanate , stereochemistry , organic chemistry , linguistics , philosophy , polyurethane
Concise and efficient synthetic route to the core of calyciphylline A‐type alkaloids is described herein. The aza‐[5,6,6] tricyclic framework of the Daphniphyllum subclass of these alkaloids was constructed featuring [1,3]‐Ichikawa transposition and intramolecular Heck cyclization protocols.