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Asymmetric Total Synthesis of (–)‐Gracilamine Using a Bioinspired Approach
Author(s) -
Chandra Atish,
Verma Prachi,
Negel Animesh,
Pandey Ganesh
Publication year - 2017
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.201701474
Subject(s) - chemistry , total synthesis , enantioselective synthesis , elaboration , biomimetic synthesis , combinatorial chemistry , organic chemistry , stereochemistry , catalysis , philosophy , humanities
The asymmetric total synthesis of optically pure (–)‐gracilamine ( 1 ) was achieved by employing a bioinspired approach. The strategy involved elaboration of 3 a ‐arylhexahydroindole 7 , a designed precursor, to 3 a ‐formylarylhexahydroindole 5 , which upon heating with l ‐leucine ethyl ester gave (–)‐ 1 efficiently.