Oxidative rearrangement of 2-alkoxy-3,4-dihydro-2H-pyrans: stereocontrolled synthesis of 4,5-cis-disubstituted tetrahydrofuranones
作者:Alan Armstrong、Hunsuk Chung
DOI:10.1016/j.tetlet.2005.12.120
日期:2006.3
Oxidation of 2-alkoxy-3,4-dihydro-2H-pyrans with dimethyldioxirane 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 13 and cognac lactone 14.
用二甲基二环氧乙烷氧化2-烷氧基-3,4-二氢-2 H-吡喃,然后进行琼斯氧化,导致4,5-顺式-二取代的四氢呋喃酮的重排和立体控制的形成;该方法适用于威士忌内酯13和白兰地内酯14的合成。