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Stereoselective Total Synthesis and Structural Elucidation of (−)‐Indoxamycins A–F
Author(s) -
He Chi,
Zhu Chenlong,
Wang Bingnan,
Ding Hanfeng
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201403986
Subject(s) - stereoselectivity , enantioselective synthesis , stereochemistry , total synthesis , chemistry , tandem , absolute configuration , enyne , michael reaction , combinatorial chemistry , organic chemistry , catalysis , materials science , composite material
In this study, a concise and stereoselective approach for the divergent total synthesis of (−)‐indoxamycins A–F is described. The key steps of the strategy include an Ireland–Claisen rearrangement, an enantioselective 1,6‐enyne reductive cyclization, and a tandem 1,2‐addition/oxa‐Michael/methylenation reaction. The relative and absolute configuration of these natural products has been unambiguously elucidated, and their cytotoxic activities against HT‐29 and A‐549 tumor cell lines are also reported.