Synthesis of Polyketide Stereoarrays Enabled by a Traceless Oxonia-Cope Rearrangement†
Lin Yang
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai 200032 (China) http://honggroup.sioc.ac.cn
These authors contributed equally to this work.
Search for more papers by this authorGuoli He
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai 200032 (China) http://honggroup.sioc.ac.cn
These authors contributed equally to this work.
Search for more papers by this authorRuifeng Yin
College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua, Zhejiang 321004 (China)
These authors contributed equally to this work.
Search for more papers by this authorDr. Lili Zhu
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai 200032 (China) http://honggroup.sioc.ac.cn
Search for more papers by this authorProf. Dr. Xiaoxia Wang
College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua, Zhejiang 321004 (China)
Search for more papers by this authorCorresponding Author
Prof. Dr. Ran Hong
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai 200032 (China) http://honggroup.sioc.ac.cn
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai 200032 (China) http://honggroup.sioc.ac.cnSearch for more papers by this authorLin Yang
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai 200032 (China) http://honggroup.sioc.ac.cn
These authors contributed equally to this work.
Search for more papers by this authorGuoli He
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai 200032 (China) http://honggroup.sioc.ac.cn
These authors contributed equally to this work.
Search for more papers by this authorRuifeng Yin
College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua, Zhejiang 321004 (China)
These authors contributed equally to this work.
Search for more papers by this authorDr. Lili Zhu
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai 200032 (China) http://honggroup.sioc.ac.cn
Search for more papers by this authorProf. Dr. Xiaoxia Wang
College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua, Zhejiang 321004 (China)
Search for more papers by this authorCorresponding Author
Prof. Dr. Ran Hong
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai 200032 (China) http://honggroup.sioc.ac.cn
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai 200032 (China) http://honggroup.sioc.ac.cnSearch for more papers by this authorFinancial support from the National Natural Science Foundation of China (No. 21290184), The MOST (2010CB833200), and Chinese Academy of Sciences are highly appreciated. We thank Wenhua Li for the kinetic resolution of the racemic allenic alcohol (rac-1 a). We also thank Dr. Rob Hoen (GP Pharm, Spain) and Dr. Jeremy R. Duvall (The Broad Institute, MA) for helpful discussions.
Abstract
Polyketide antibiotics bearing skipped polyols represent a synthetic challenge. A SiCl4-promoted oxonia-Cope rearrangement of syn,syn-2-vinyl-1,3-diols was developed to forge an array of 1,5-pentenediols, thus providing versatile motifs for the preparation of 1,2,3,5-stereoarrays in a highly stereoselective manner. Further exploration with Sn(OTf)2 realized the rearrangement of a cross-aldehyde which tactically warrants the utility of the current approach to access complex polyketides. The origin of high stereoselectivity is attributed to a chairlike anti-conformation of the oxonium ion intermediate.
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