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Eine neuartige Fragmentierung bicyclischer Enoläther Verfahren zur Darstellung macrocyclischer Lactone
Author(s) -
Becker J.,
Ohloff G.
Publication year - 1971
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19710540854
Subject(s) - chemistry , homolysis , enol , yield (engineering) , vicinal , lactone , fragmentation (computing) , stereochemistry , medicinal chemistry , organic chemistry , radical , catalysis , metallurgy , computer science , operating system , materials science
Vicinal α‐hydroperoxy‐tetrahydropyranyl ethers annelated to cyclododecane are smoothly converted by homolytic fission in about 75% yield to a mixture of the macrocyclic lactones 3 , 4 , and 5. Based on this observation, an economically feasible synthesis of Exaltolide 1 (>65% yield) has been developed. The mechanism of this new β‐fragmentation reaction is discussed.