Two remarkable epimerizations imperative for the success of an asymmetric total synthesis of (+)-aigialospirol |
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| Authors: | FIGUEROA Ruth FELTENBERGER John B. GUEVARRA Christle C. & HSUNG Richard P. Division of Pharmaceutical Sciences |
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| Affiliation: | FIGUEROA Ruth 1,FELTENBERGER John B.1,GUEVARRA Christle C.1 & HSUNG Richard P.1,2 1 Division of Pharmaceutical Sciences and Department of Chemistry,University of Wisconsin,Madison,WI 53705,USA 2School of Pharmaceutical Science and Technology,Tianjin University,Tianjin 300072,China |
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| Abstract: | Two remarkable epimerization processes were uncovered during our pursuit of an enantioselective synthesis of(+)-aigialospirol featuring a cyclic acetal tethered ring-closing metathesis.Through modeling,we were able to turn these two unexpected epimerizations to our advantage via modeling to ensure a successful and concise total synthesis,thereby firmly establishing cyclic acetal tethered RCM as a powerful strategy in natural product synthesis.Most importantly,calculations allowed us to fully understand the ... |
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| Keywords: | cyclic acetal tethered RCM ( )-aigialospirol anomeric effect and epimerization. |
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