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Total Synthesis of Divergolides E and H
Author(s) -
Caplan Scott M.,
Floreancig Paul E.
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201810336
Subject(s) - ketene , chemistry , acetal , aniline , bicyclic molecule , amide , stereochemistry , cleavage (geology) , total synthesis , combinatorial chemistry , organic chemistry , materials science , composite material , fracture (geology)
This manuscript describes the first total syntheses of divergolides E and H. The route employs a telescoped hetero‐Diels–Alder and oxidative carbon–hydrogen bond cleavage as an entry into the central bridged bicyclic acetal unit. Additional key steps of the highly convergent route include a desymmetrizing epoxidation, a chelation‐controlled alkenylzinc addition, an amide formation between a hindered aniline and an acylating agent that is prone to ketene formation, and a challenging macrolactonization.