| Literature DB >> 29286556 |
Joyce C Leung1, Aaron A Bedermann1, Jón T Njardarson1, David A Spiegel1, Graham K Murphy1, Naoto Hama1, Barry M Twenter1, Ping Dong1, Tatsuya Shirahata1, Ivar M McDonald1, Munenori Inoue1, Nobuaki Taniguchi1, Travis C McMahon1, Christopher M Schneider1, Nancy Tao1, Brian M Stoltz1, John L Wood1.
Abstract
Described herein is a synthetic strategy for the total synthesis of (±)-phomoidride D. This highly efficient and stereoselective approach provides rapid assembly of the carbocyclic core by way of a tandem phenolic oxidation/intramolecular Diels-Alder cycloaddition. A subsequent SmI2 -mediated cyclization cascade delivers an isotwistane intermediate poised for a Wharton fragmentation that unveils the requisite bicyclo[4.3.1]decene skeleton and sets the stage for synthesis completion.Entities:
Keywords: bicyclic compounds; cycloaddition; natural products; oxidation; total synthesis
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Year: 2018 PMID： 29286556 DOI： 10.1002/anie.201712369
Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336