ChemInform Abstract: Oxidative Rearrangement of 2-Alkoxy-3,4-dihydro-2H-pyrans: Stereocontrolled Synthesis of 4,5-cis-Disubstituted Tetrahydrofuranones Including Whisky and Cognac Lactones and Crobarbatic Acid

Autor:	Hunsuk Chung, Cassim Ashraff, Alan Armstrong, Lorraine Murtagh
Rok vydání:	2009
Předmět:	chemistry.chemical_classification Jones oxidation chemistry.chemical_compound chemistry Alkoxy group Urea General Medicine Oxidative phosphorylation Dimethyldioxirane Medicinal chemistry Lactone
Zdroj:	ChemInform. 40
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200939101
Popis:	Oxidation of 2-alkoxy-3,4-dihydro-2H-pyrans 3 with dimethyldioxirane or MTO/urea–H2O2 followed by Jones oxidation leads to rearrangement and stereocontrolled formation of 4,5-cis-disubstituted tetrahydrofuranones. The method is applied to the synthesis of the whisky lactone 9, cognac lactone 10 and crobarbatic acid 17.
Databáze:	OpenAIRE
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