Synthesis of a mixture of (2S,5R)- and (2S,5S)-2-methyl-1,6-dioxaspiro[4.5]decane, the odor bouquet minor components of Paravespula vulgaris (L.), from L-sorbose

Article abstract of DOI:10.1016/0008-6215(94)00320-F

The synthesis of (2S,5RS)-2-methyl-1,6-dioxaspiro[4.5]decane (1) from (2S,4S,5R)- (26) and (2S,4S,5S)-4-hydroxy-2-methyl-1,6-dioxaspiro[4.5]decane (27), obtained in thirteen and fourteen steps from L-sorbose by two convergent syntheses, has been accomplished using Wittig methodology, Barton deoxygenation, reduction, and spiroketalation of the appropriately protected derivatives.