2396-65-8Relevant articles and documents
Total Synthesis of (±)-Phomoidride D
Leung, Joyce C.,Bedermann, Aaron A.,Njardarson, Jón T.,Spiegel, David A.,Murphy, Graham K.,Hama, Naoto,Twenter, Barry M.,Dong, Ping,Shirahata, Tatsuya,McDonald, Ivar M.,Inoue, Munenori,Taniguchi, Nobuaki,McMahon, Travis C.,Schneider, Christopher M.,Tao, Nancy,Stoltz, Brian M.,Wood, John L.
, p. 1991 - 1994 (2018)
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.
Toward the synthesis of phomoidride D
Murphy, Graham K.,Shirahata, Tatsuya,Hama, Naoto,Bedermann, Aaron,Dong, Ping,McMahon, Travis C.,Twenter, Barry M.,Spiegel, David A.,McDonald, Ivar M.,Taniguchi, Nobuaki,Inoue, Munenori,Wood, John L.
, p. 477 - 489 (2013/03/14)
An efficient and highly stereoselective approach toward the phomoidride family of natural products is described. The carbocyclic core structure was assembled using a tandem phenolic oxidation/Diels-Alder cycloaddition and a tandem 5-exo-trig/5-exo-trig radical cyclization to deliver an isotwistane intermediate that, upon a late-stage xanthate-initiated Grob fragmentation, furnishes the requisite bicyclo[4.3.1]decene.
