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

Autor:	Werner Löwe, Joachim Buddrus, Peter Luger, Manuela Weber, Stefanie A. Brätter
Rok vydání:	2001
Předmět:	Tetraethylene glycol chemistry.chemical_compound chemistry Yield (chemistry) Organic Chemistry Methanol 4-Pyrone Ring (chemistry) Favorskii rearrangement Medicinal chemistry Sodium methoxide Derivative (chemistry)
Zdroj:	Journal of Heterocyclic Chemistry. 38:365-370
ISSN:	1943-5193 0022-152X
DOI:	10.1002/jhet.5570380208
Popis:	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 k with a carbenium-oxonium-ion subunit (Scheme 3). The structure of the 3(2H)-furanone derivative was confirmed by X-ray analysis.
Databáze:	OpenAIRE
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