Total synthesis of reblastatin.
Enantioselective total synthesis of reblastatin is described. The synthesis highlights hydrozirconation, transmetalation, aldehyde addition sequence to install E-trisubstituted olefin and C7 stereocenter, and the first use of an intramolecular Buchwald-like amidation reaction to close the 19-membered macrolactam.
Wrona
Iwona E
IE
Department of Chemistry, Boston University, Boston, Massachusetts 02215, USA.
Gabarda
Ana E
AE
Evano
Gwilherm
G
Panek
James S
JS
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D007202:Indicators and Reagents; D008956:Models, Chemical; D011809:Quinones / Q000138:chemical synthesis*
D000900:Anti-Bacterial Agents; D007202:Indicators and Reagents; D011809:Quinones; C414123:reblastatin