Total synthesis of (+)-lepadin F.
An enantioselective total synthesis of (+)-lepadin F is described. The synthetic sequence features an intermolecular aza-[3 + 3] annulation, homologation of a vinylogous amide via Eschenmoser's episulfide contraction, and a highly stereoselective hydrogenation essential for achieving the 1,3-anti relative stereochemistry at C2 and C8a.
Li
Gang
G
Division of Pharmaceutical Sciences and Department of Chemistry, 777 Highland Avenue, University of Wisconsin, Madison, Wisconsin 53705, USA.
Hsung
Richard P
RP
Slafer
Brian W
BW
Sagamanova
Irina K
IK
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000145:classification; D000475:Alkenes / Q000737:chemistry; D000577:Amides / Q000737:chemistry; D018360:Crystallography, X-Ray; D006859:Hydrogen / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000145:classification
D000470:Alkaloids; D000475:Alkenes; D000577:Amides; D011804:Quinolines; C455162:lepadin F; D006859:Hydrogen