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Total Synthesis of (−)‐4‐ epi ‐Englerin A
Author(s) -
Kumar Palli Kishore,
Reddy Anugu Raghunath,
Chandrasekhar Srivari
Publication year - 2021
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.202100354
Subject(s) - chemistry , sharpless asymmetric dihydroxylation , aldol reaction , epimer , epoxide , natural product , total synthesis , stereochemistry , dihydroxylation , sharpless epoxidation , enantioselective synthesis , metathesis , aldol condensation , limonene , organic chemistry , catalysis , polymer , polymerization , chromatography , essential oil
The synthesis of (−)‐4‐ epi ‐Englerin A, the epimer of natural product (−)‐Englerin A, a sesquiterpenoid with exceptional anti‐proliferative activity in renal cancer cells is achieved from ( R )‐(+)‐limonene. Key features of the synthesis are Sharpless asymmetric dihydroxylation, aldol reaction, and transannular epoxide opening reactions to install the required functionalities of oxabridged tricyclic core.