Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 21, Pages 7090-7093Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201601319
Keywords
alkaloid; chiral auxiliary; desymmetrization; hypervalent iodine; total synthesis
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Funding
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- Canada Foundation for Innovation (CFI)
- provincial government of Quebec (FQRNT)
- provincial government of Quebec (CCVC)
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The first enantioselective synthesis of (-)-strychnopivotine from a known and inexpensive phenol has been achieved in 15 steps. The strategy is based on a new diastereoselective aza-Michael-enol-ether cascade desymmetrization of a dienone, guided by a removable lactic acid-derived chiral auxiliary. Synthesis involves a phenol dearomatization, a conjugated silicon addition, a stereoselective double reductive amination, and two Heck-type carbopalladations as key steps. The absolute configuration of the natural compound, which, to date, has been uncertain, was confirmed by using circular dichroism (CD) spectroscopy and X-ray analyses.
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