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Total Synthesis of Epicolactone
Author(s) -
Kravina Alberto G.,
Carreira Erick M.
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201807709
Subject(s) - intramolecular force , total synthesis , cyclobutane , natural product , chemistry , regioselectivity , stereochemistry , reactivity (psychology) , diene , ring (chemistry) , cyclobutanes , metabolite , secondary metabolite , quinone , combinatorial chemistry , organic chemistry , catalysis , biochemistry , medicine , natural rubber , alternative medicine , pathology , gene
The biologically active and structurally complex secondary metabolite epicolactone is a member of the natural product pool found in cash crop endophytes of the genus Epicoccum . By exploiting inherent reactivity, a total synthesis of this highly oxygenated and polycyclic molecule met chemo‐ and regioselectivity challenges. The key buildup of complexity was accomplished via an intramolecular [2+2] photocycloaddition between a quinone and an electron‐deficient diene followed by a cyclobutane ring expansion. The use of a dioxene as an acyl anion equivalent and an intramolecular carbonyl methenylation furnished the natural product.