Efficient enantioselective synthesis of (+)-sclareolide and (+)-tetrahydroactinidiolide: chiral LBA-induced biomimetic cyclization |
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Authors: | Kiran B Upar Sanjay J Mishra Shrikant P Nalawade Soni A Singh Reena P Khandare Sujata V Bhat |
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Institution: | aLaboratory for Advanced Research in Natural and Synthetic Chemistry, V. G. Vaze College, Mumbai University, Mithagar Road, Mulund (East), Mumbai 400 081, India |
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Abstract: | An efficient enantioselective synthesis of the lactones (+)-sclareolide and (+)-tetrahydroactinidiolide has been achieved through Lewis acid-assisted chiral Brønsted acid-induced enantioselective cyclization of terpenic carboxylic acids. The reaction sequence involved the 2,3] sigmatropic rearrangement of an allylic alcohol and biomimetic cyclization of terpenic acid in the presence of (R)-2-benzyloxy-2′-hydroxy-1,1′-binaphthyl and tin tetrachloride as key steps. The cyclization gave lactones in good yield and with high enantiomeric excess. |
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