Enantioselective synthesis of imperanene via enzymatic asymmetrization of an intermediary 1,3-diol.
[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.
Carr
Jason A
JA
Department of Chemistry, University of South Florida, Tampa, Florida 33620, USA.
Bisht
Kirpal S
KS
D001547:Benzaldehydes / Q000737:chemistry*; D016956:Burkholderia cepacia / Q000201:enzymology*; D002384:Catalysis; D008049:Lipase / Q000378:metabolism*; D015394:Molecular Structure; D010636:Phenols / Q000032:analysis / Q000138:chemical synthesis*; D013237:Stereoisomerism
D001547:Benzaldehydes; D010636:Phenols; C093767:imperanene; C100058:vanillin; D008049:Lipase