HCID 70511091, compound → HCID 86737361, compound

Participants

Reaction Steps

A mixture of 5-[(2RS,3SR)-3-hydroxy-6-[(E)-2-hydroxyethylidene]-2-methyl-2-oxepanyl]-2-methyl-1-(tetrahydropyran-2-yloxy)pentane (953 mg, 2.67 mM), manganese dioxide (4 g) and methylene chloride (20 ml) is stirred for three days at room temperature under nitrogen. The mixture is filtered through a pad of Celite and washed with methylene chloride (2×30 ml). The solvent is removed in vacuo and the residue purified by column chromatography on silica gel (15 g) with 30% ether in petroleum ether to give (1RS,4SR,5RS)-4-methyl-4-[4-methyl-5-(tetrahydropyran-2-yloxy)pentyl]-3,8-dioxabicyclo [3.2.1] octane-1-acetaldehyde (0.813 g, 73%) as a colorless oil.

Provenance & Evidence