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Four diastereomers of the insecticide iridomyrmecin are prepared in five steps from naturally occurring nepetalactones, which are isolated from catnip oil.

3(S)-Hydroxy-Leukotriene B 4 ( 1a ), its 3(R)-epimer 1b , and a 14,15-acetylenic analogue were efficiently prepared via chelation-controlled reduction of ketone 12 , obtained by acetylide addition to chiral β-hydroxylactones 7/9 .

The type IIB eicosanoids, 12(R),20- and 12(S),20-dihydroxyeicosatetraenoic acid (DiHETE), were conveniently synthesized utilizing a carbohydrate-derived bis-lactol as a differentiated 4-hydroxyhex-2(E)-enedial chiron. 12(S),20-DiHETE, but not the 12(R)-isomer, induced vasodilation in precontracted canine arteries.

A differentiated, six-carbon vicinal -diol chiron was prepared from D -glucurono-6,3-lactone and exploited in the asymmetric synthesis of the erythro/threo -isomers of the title eicosanoids.