Total synthesis of iejimalide B. An application of the Shiina macrolactonization.
The potent anticancer compound iejimalide B (1) was prepared by a total synthesis through a strategy that features Julia olefinations, Wittig olefinations, a Carreira enantioselective alkynylation, a Heck reaction, a Marshall propargylation reaction, a Stille coupling, and a Shiina macrolactonization.
Schweitzer
Dirk
D
Department of Chemistry and Biochemistry and Walther Cancer Research Center, University of Notre Dame, Notre Dame, Indiana 46556, USA.
Kane
John J
JJ
Strand
Daniel
D
McHenry
Peter
P
Tenniswood
Martin
M
Helquist
Paul
P
D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D002219:Carbamates / Q000138:chemical synthesis*; D018942:Macrolides / Q000138:chemical synthesis*; D015394:Molecular Structure
D000970:Antineoplastic Agents; D002219:Carbamates; D018942:Macrolides; C520301:iejimalide B