Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 15, Pages 3572-3576Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201700476
Keywords
actinoranone; meroterpenoid; natural products; stereochemistry; total synthesis
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Funding
- Shenzhen Peacock Plan [KQTD2015071714043444]
- NSFC [21572007, 21272011, 21133002]
- SZSTDF [JCYJ20160527100424909, JCYJ20150629144022829, JSGG 20160608091824706, 20140717102922014]
- GDNSF [2014A030312004, 2014B030301003]
- Fong Shu Fook Tong Foundation
- Joyce M. Kuok Foundation
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The total synthesis of four actinoranone stereoisomers led to unambiguous assignment of relative and absolute stereochemistry of the natural product. Key features of the convergent, fully stereocontrolled route include the use of a Negishi carbozirconation/iodination, a Friedel-Crafts cyclization, a Felkin-controlled addition reaction, a Mitsunobu reaction, and a late-stage C-H oxidation.
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