Tetrahedron p. 3413 - 3428 (1992)
Update date:2022-07-30
Topics:
Baldwin, Jack E.
Adlington, Robert M.
Ramcharitar, Steve H.
Intramolecular free-radical addition to propiolate esters has provided a new and stereoselective route to 14-16 membered trans-α,β-unsaturated macrocyclic lactones from their corresponding ω-iodoalkyl-propiolate esters under triphenyltin hydride/AIBN mediated conditions.Attempts to synthesise analogous 10-13 membered lactones proved unsuccessful, resulting in acyclic products derived from direct reduction at the radical centre. Key words: Radical; macrocyclisation; propiolate ester; macrocyclic unsaturated lactone; high dilutionm
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