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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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201712369
Subject(s) - total synthesis , stereoselectivity , tandem , intramolecular force , cycloaddition , stereochemistry , bicyclic molecule , cascade , chemistry , fragmentation (computing) , cascade reaction , combinatorial chemistry , organic chemistry , computer science , catalysis , programming language , materials science , chromatography , composite material
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.