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Stereoselective Total Synthesis of (‐)‐Ebelactone A
Author(s) -
Srinivasu Khandregula,
Nagaiah Kommu,
Yadav Jhillu S.
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201904949
Subject(s) - stereoselectivity , desymmetrization , total synthesis , wittig reaction , hydroboration , stereochemistry , chemistry , alkylation , olefin fiber , bicyclic molecule , diol , enantioselective synthesis , organic chemistry , catalysis
A highly stereoselective total synthesis of the β ‐lactam inhibitor of several therapeutically important enzymes, (‐)‐ebelactone A ( 1 ) is described. The salient features of this synthesis include desymmetrization of bicyclic symmetric olefin with Brown's asymmetric hydroboration, Wittig olefination, Evans′ alkylation, Sharpless asymmetric epoxidation, Gillman's reaction, TEMPO‐BAIB mediated selective oxidation of 1,3‐diol and Adam's β ‐lactonization.