Tetrahedron

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

A Armstrong, C Ashraff, H Chung, L Murtagh

文献索引：Armstrong, Alan; Ashraff, Cassim; Chung, Hunsuk; Murtagh, Lorraine Tetrahedron, 2009 , vol. 65, # 23 p. 4490 - 4504

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被引用次数: 8

摘要

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.