Syntheses in the Fumagillin series

Abstract

Two approaches to syntheses in the fumagillin series have been covered. a): The synthesis of 1,4-dioxaspiro [4,5]dec-7-ene has been achieved and may prove useful in the preparation of 2-methoxycyclohexanols as found in the fumagillin series. b): The reaction of excess of Grignard reagent with the lactones cis- and trans-octahydrobenzofuran-2-one can lead to a new synthesis of previously known compounds such as 6-(2'-methylpropenyl)-1,4-dioxaspiro[4,5]decane and cis- and trans-2,2-dimethyloctahydrobenzofuran. The stereochemistry of the various products in the synthetic scheme has been established and the approach has been shown to provide a possible route, using different Grignard reagents, to the fumagillin series.