Enantioselective Synthesis of Imperanene via Enzymatic Asymmetrization of an Intermediary 1,3-Diol

Abstract

[reaction: see text] Using a chemoenzymatic synthetic strategy, (S)-imperanene and its (R)-enantiomer has been synthesized from vanillin in nine steps. The key step in the synthesis involves the use of Pseudomonas cepacia lipase (PS-30) to induce asymmetrization of the intermediary prochiral 1,3-diol in >97% ee.

Design, asymmetric synthesis, and evaluation of pseudosymmetric sulfoximine inhibitors against HIV-1 protease

“…The enantiomeric purity was subsequently checked by derivatizing with Mosher's reagent and no racemization was observed. The acetate group in 6 was removed by treatment with K 2 CO 3 in MeOH 16 to afford intermediate 7. The primary alcohol in 7 was subsequently oxidized by Jones' reagent 17 to afford the carboxylic acid compound 8 with the desired stereochemistry (Scheme 2).…”

Chiral recognition of imperanene enantiomers by various cyclodextrins: A capillary electrophoresis and NMR spectroscopy study

“…Racemic and enantiopure Ipn has been synthesized and characterized by various methods so far [11][12][13][14][15][16]. In these studies, the enantiomeric excess was solely determined by HPLC using either a Chiralcel OD-H, Chiralpak AD-RH, or (R,R)-Whelk-O 1 chiral analytical column coupled to UV detection at 254 nm [12][13][14]16].…”

Stereoselective Enzymatic Acylations (Transesterifications)

“…Both enantiomers of imperanene, a phenolic natural product, have been synthesized from vanillin, using a chemoenzymatic synthetic strategy [151]. The key step involves the use of PCL to induce asymmetrization of the intermediary prochiral 1,3-diol 19, Fig.…”