Diastereoselective synthesis of (+)-nephrosterinic acid and (+)-protolichesterinic acid |
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| Authors: | Rodney A Fernandes Mahesh B Halle Asim K Chowdhury Arun B Ingle |
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| Institution: | Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400 076, Maharashtra, India |
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| Abstract: | A diastereoselective synthesis of (+)-nephrosterinic acid and (+)-protolichesterinic acid, common members of the paraconic acids is described. The synthesis is based on a diastereoselective orthoester Johnson–Claisen rearrangement of a (Z)-allyl alcohol with a vicinal dioxolane moiety as key steps. The synthesis is completed in 10 steps and with overall yields of 15.9% for (+)-nephrosterinic acid and 16.4% for (+)-protolichesterinic acid. |
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