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Total Synthesis of (±)‐Phomoidride D |
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| Authors: | Dr. Joyce C. Leung Dr. Aaron A. Bedermann Prof. Jón T. Njardarson Prof. David A. Spiegel Prof. Graham K. Murphy Dr. Naoto Hama Dr. Barry M. Twenter Dr. Ping Dong Prof. Tatsuya Shirahata Dr. Ivar M. McDonald Dr. Munenori Inoue Dr. Nobuaki Taniguchi Dr. Travis C. McMahon Dr. Christopher M. Schneider Dr. Nancy Tao Prof. Brian M. Stoltz Prof. John L. Wood |
| Affiliation: | Department of Chemistry and Biochemistry, Baylor University, Waco, TX, USA |
| 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. |
| Keywords: | bicyclic compounds cycloaddition natural products oxidation total synthesis |