Oxidative rearrangement of 2-alkoxy-3,4-dihydro-2 H-pyrans: stereocontrolled synthesis of 4,5-cis-disubstituted tetrahydrofuranones including whisky and cognac lactones and crobarbatic acid

Alan Armstrong,Cassim Ashraff,Hunsuk Chung,Lorraine Murtagh

doi:10.1016/j.tet.2009.04.013

Oxidative rearrangement of 2-alkoxy-3,4-dihydro-2 H-pyrans: stereocontrolled synthesis of 4,5-cis-disubstituted tetrahydrofuranones including whisky and cognac lactones and crobarbatic acid

Alan Armstrong, Cassim Ashraff + Show 2 more

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https://doi.org/10.1016/j.tet.2009.04.013

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Journal: Tetrahedron	Publication Date: Apr 10, 2009
Citations: 16

Affiliation: Imperial College London, Pfizer (United Kingdom)

#Cognac Lactone #Synthesis Of Lactone + Show 3 more

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Abstract

Oxidation of 2-alkoxy-3,4-dihydro-2 H-pyrans 3 with dimethyldioxirane or MTO/urea–H 2O 2 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.

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