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J Org Chem ; 84(24): 15997-16002, 2019 12 20.
Article in English | MEDLINE | ID: mdl-31746213

ABSTRACT

Enantioselective synthesis of ampelomin B and epi-ampelomin B, D, and E was accomplished starting from toluene, through a chemoenzymatic sequence, in which stereoselective hydrogenation, Mitsunobu reaction, and regio- and stereoselective nucleophilic opening of an epoxide were used as the main transformations. Structural revision and absolute configuration of the natural compounds were carried out.


Subject(s)
Ascomycota/chemistry , Cyclohexanes/chemical synthesis , Epoxy Compounds/chemical synthesis , Flavonoids/chemical synthesis , Cyclohexanes/chemistry , Molecular Structure , Stereoisomerism
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