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First Stereoselective Total Synthesis of Ligraminol E
Author(s) -
Gangar Mukesh,
Goyal Sandeep,
Hathiram Vankodoth,
Ramdas Wasnik Ashik,
Rao Vajja Krishna,
Nair Vipin A.
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201601411
Subject(s) - stereoselectivity , total synthesis , alkylation , chemistry , isopropyl , yield (engineering) , bromide , chiral auxiliary , alcohol , stereochemistry , isopropyl alcohol , enantioselective synthesis , organic chemistry , catalysis , materials science , metallurgy
Stereoselective total synthesis of Ligraminol E has been achieved in 8 steps in 23.9 % overall yield by employing an imidazolidinone based chiral auxiliary. The key steps involved in the synthesis are the asymmetric glycolate alkylation of ( R )‐3‐(2‐(benzyloxy)acetyl)‐4‐isopropyl‐1‐(( S )‐1‐phenylethyl)imidazo‐lidin‐2‐one with substituted benzyl bromide and the Mitsonobu reaction of a secondary alcohol and phenolic group.