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Total Syntheses of All the Amathaspiramides
Author(s) -
Chiyoda Koji,
Shimokawa Jun,
Fukuyama Tohru
Publication year - 2012
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.201109221
Subject(s) - moiety , common core , total synthesis , computer science , imine , reagent , stereochemistry , chemistry , core (optical fiber) , combinatorial chemistry , organic chemistry , telecommunications , catalysis
Six in one blow : Total syntheses of all the amathaspiramide alkaloids have been accomplished. Rapid construction of the diazaspiro[3.3]nonane core combined with regio‐ and diastereoselective reduction of the cyclic imide moiety with DIBAL established the route to the common structural motif. The late‐stage reduction of the lactam to an imine functionality mediated by Schwartz's reagent was the key to the streamlined syntheses.