A novel separation technique of diastereomeric esters of pyridylethanols by extraction: formal total synthesis of PNU-142721, HIV-1 reverse transcriptase inhibitor |
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| Authors: | Masato Matsugi Masatomo Nojima Yasuyuki Kita |
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| Affiliation: | a Department of Materials Chemistry and Frontier Research Center, Graduate School of Engineering, Osaka University, 2-1, Yamada-oka, Suita, Osaka 565-0871, Japan
b Graduate School of Pharmaceutical Sciences, Osaka University, 1-6, Yamada-oka, Suita, Osaka 565-0871, Japan |
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| Abstract: | The separation of diastereomeric esters derived from (±)-pyridylethanols and 3β-acetoxyetienic acid were achieved by an extraction technique using diethyl ether and aqueous hydrochloric acid. A formal total synthesis of PNU-142721 was effectively carried out to prepare the chiral, non-racemic synthon 1-furo[2,3-c]pyridin-5-yl-ethanol (1) by means of this technique. The structure optimized using MOPAC calculations on each diastereomer suggested the presence of intramolecular CH/π interaction in only the (S)-isomer of the diastereomers. |
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| Keywords: | Chiral resolution CH/π interaction Diastereomers Extraction PNU-142721 |
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