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Total Synthesis of (±)‐Phomoidride D
Author(s) -
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.
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201712369
Subject(s) - total synthesis , stereoselectivity , tandem , intramolecular force , cycloaddition , chemistry , bicyclic molecule , stereochemistry , combinatorial chemistry , cascade , fragmentation (computing) , cascade reaction , organic chemistry , catalysis , computer science , materials science , chromatography , composite material , operating system
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 SmI 2 ‐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.