Total synthesis of (+/-)-lepadiformine via an amidoacrolein cycloaddition.
[reaction: see text]. The total synthesis of the cytotoxin lepadiformine is described. The intermolecular cycloaddition of a 2-amidoacrolein with the dimethyl acetal of 4,6-heptadienal gave a cycloadduct that was strategically functionalized for elaboration of the tricyclic ring system. These steps include a diastereoselective addition of an organoytterbium reagent to an aldehyde, cyclization to the trans-perhydroquinoline substructure via a Mitsunobu reaction, and an iodine-promoted amine cyclization with an alkene to introduce the pyrrolidine ring.
Greshock
T J
TJ
Department of Chemistry, Pennsylvania State University, University Park, Pennsylvania 16802, USA.
Funk
R L
RL
D000171:Acrolein / Q000031:analogs & derivatives* / Q000737:chemistry*; D000470:Alkaloids / Q000138:chemical synthesis*; D000818:Animals; D002317:Cardiovascular Agents / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D003500:Cyclization; D007202:Indicators and Reagents; D013237:Stereoisomerism; D014561:Urochordata / Q000737:chemistry*
D000470:Alkaloids; D002317:Cardiovascular Agents; D007202:Indicators and Reagents; C431548:lepadiformine; D000171:Acrolein