First Stereoselective Total Synthesis of Ligraminol E | Zendy

Gangar Mukesh | Zendy; Goyal Sandeep | Zendy; Hathiram Vankodoth | Zendy; Ramdas Wasnik Ashik | Zendy; Rao Vajja Krishna | Zendy; Nair Vipin A. | Zendy

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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.

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