2-Hexyl-4-acetoxytetrahydrofuran is a flavor compound with a sweet, floral-fruity odour. Two different methods for its preparation were investigated starting from 1-decen-4-ol. 1-Decen-4-ol was transformed to 2-hexyl-4-acetoxytetrahydrofuran through mesylation, dihydroxylation, intramolecular nucleophilic substitution and acetylation in overall 70% yield; alternatively, 1-decen-4-ol was epoxidised to 1,2-epoxy-4-decanol, followed by acetylation and dehydration to produce the desired product in overall 48% yield. The two methods gave the product with poor and opposite diastereoselectivity but both routes have advantages on yield or ease of operation over the literature procedure.

The four stereoisomers of 2-hexyl-4-acetoxytetrahydrofuran were prepared starting from (R)-or (S)-1-decen-4-ol (>96% ee). They were obtained by kinetic resolution of racemic homoallylic alcohol catalysed by Novozym 435 (Candida antarctica). (R)-or (S)-1-Decen-4-ol proceeded Sharpless asymmetric dihydroxylation (AD) using AD-mix-α or β as an oxidant followed by ring closure to afford cis-2-hexyl-4-hydroxytetrahydrofuran as the major product with 50-60% de. The diastereomers were separated by derivatization to the corresponding p-nitrobenzoates, and the ee values of cis-isomers were determined by chiral HPLC to be >96%. A pair of enantiomers of cis-2-hexyl-4-hydroxytetrahydrofuran was produced by hydrolysis of the corresponding p-nitrobenzoate, respectively. The four stereoisomers of 2-hexyl-4-acetoxytetrahydrofuran were obtained with >95% ee values from (2S,4R)-or (2R,4S)-cis-2-hexyl-4-hydroxytetrahydrofuran by direct acylation with acetic anhydride or Mitsunobu reaction with acetic acid in the presence of Ph 3 P and diisopropyl azodicarboxylate. The four stereoisomers presented very distinct differences in both feature and intensity.

Two alternative routes for the synthesis of the title furan (VI), a flavor compound with a sweet, floral‐fruity odour, starting from decen‐4‐ol (I) are developed.