The chemistry of the highly reactive 2,6-bis (bromomethyl)-4-pyrone

Under basic conditions 2,6-bis(bromomethyl)-4-pyrone 8 reacts with tetraethylene glycol to yield the unexpected macrocycle 9, which is related to the antibiotic Kjellmanianone 10. We propose that this ring transformation proceeds via the cyclopropyl intermediate d (Scheme 2), which undergoes a ring...

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Bibliographic Details
Published inJournal of heterocyclic chemistry Vol. 38; no. 2; pp. 365 - 370
Main Authors Lowe, W, Bratter, SA, Weber, M, Luger, P, Buddrus, J
Format Journal Article
LanguageEnglish
Published ODESSA HETERO CORPORATION 01.03.2001
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:Under basic conditions 2,6-bis(bromomethyl)-4-pyrone 8 reacts with tetraethylene glycol to yield the unexpected macrocycle 9, which is related to the antibiotic Kjellmanianone 10. We propose that this ring transformation proceeds via the cyclopropyl intermediate d (Scheme 2), which undergoes a ring opening reaction comparable to the Favorskii rearrangement. Also, 8 reacts with methanol/sodium methoxide to yield the 3(2H)-furanone derivative 11, the formation of which is suggested to proceed via the intermediate ii with a carbenium-oxonium-ion subunit (Scheme 3). The structure of the 3(2H)-furanone derivative was confirmed by X-ray analysis.
ISSN:0022-152X
DOI:10.1002/jhet.5570380208