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Divergent Total Synthesis of Indoxamycins A, C, and F
Author(s) -
He Chi,
Zhu Chenlong,
Dai Zhifeng,
Tseng ChihChung,
Ding Hanfeng
Publication year - 2013
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.201307426
Subject(s) - computer science , key (lock) , world wide web , computer security
The concise and divergent total synthesis of (−)‐indoxamycins A, C, and F has been completed for the first time by using a tricyclic enone as the common late‐stage intermediate. The key steps of the strategy are based on an Ireland–Claisen rearrangement, a stereodivergent reductive 1,6‐enyne cyclization, and a tandem 1,2‐addition/oxa‐Michael/methylenation reaction.