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Enantiospecific Total Synthesis of (−)‐Bengamide E
Author(s) -
Metri Prashant K.,
Schiess Raphael,
Prasad Kavirayani R.
Publication year - 2013
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201200999
Subject(s) - desymmetrization , total synthesis , tartaric acid , amide , chemistry , natural product , organic chemistry , stereochemistry , enantioselective synthesis , catalysis , citric acid
Total synthesis of the polyhydroxy caprolactam amide natural product, bengamide E, is accomplished starting from tartaric acid. Key reactions in the synthesis include desymmetrization of the bis(dimethylamide) unit of tartaric acid, Zn(BH 4 ) 2 ‐mediated anti ‐selective reduction, and a Horner–Wadsworth–Emmons olefination .
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