Abstract
The natural product chemistry of opisthonotal gland excretion was studied for the mold mite Tyrophagus putrescentiae. The secretion contained a new type of monoterpene dial, 2(E)(4-inethyl-3-pentenylidene)-butanedial (1), which we gave the trivial name β-acaridial. The compound was synthesized by a Wittig reaction of 4-methyl-3-pentenyltriphenylphosphonium bromide with 1, 4-tetrahydropyranoxy-2-oxobutane (derived from the hydration of 2-butyn-l, 4-diol with HgSO4 and H2SO4, and subsequent protection of the hydroxy groups as tetrahydropyranoxy ether), deprotection of the hydroxy groups, and subsequent oxidation with PDC. The synthetic dialcohol was identical to β-acaridiol obtained by the reduction of the natural product.
