Eine neuartige Fragmentierung bicyclischer Enoläther Verfahren zur Darstellung macrocyclischer Lactone | Zendy

Becker J. | Zendy; Ohloff G. | Zendy

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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.

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