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Divergent Total Syntheses of Lyconadins A and C
Author(s) -
Yang Yang,
Haskins Christopher W.,
Zhang Wandi,
Low Pui Leng,
Dai Mingji
Publication year - 2014
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.201400416
Subject(s) - total synthesis , mannich reaction , tandem , chemistry , stereochemistry , divergent synthesis , combinatorial chemistry , core (optical fiber) , organic chemistry , computer science , catalysis , materials science , telecommunications , composite material
Divergent and concise total syntheses of two lycopodium alkaloids, lyconadins A and C have been developed. The synthesis of lyconadin A, having potent neurotrophic activity, features an efficient one‐pot ketal removal and formal aza‐[4+2] cyclization to form the cagelike core structure. A tandem ketal removal/Mannich reaction was developed to build the tricyclic structure of lyconadin C. Both lyconadins A and C were synthesized from a pivotal intermediate.