Total synthesis of the marine alkaloid (+/-)-lepadiformine via a radical carboazidation.
[reaction: see text] The total synthesis of lepadiformine has been achieved in 10 steps and 15% overall yield from cyclohexanone. The amino-substituted quaternary carbon center is created through a radical carboazidation reaction. The tricyclic core of lepadiformine is built via an efficient hydrogenation process, involving reduction of the azide and intramolecular reductive amination of a ketone, followed by lactamization of the intermediate gamma-aminoester. The hydroxymethyl side chain is introduced according to a modified Takahata procedure after conversion of the lactam into a thiolactam.
Schär
Pascal
P
Departement für Chemie und Biochemie, Universität Bern, Freiestrasse 3, CH-3012 Bern, Switzerland.
Renaud
Philippe
P
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D003512:Cyclohexanones / Q000737:chemistry*; D008386:Marine Biology; D015394:Molecular Structure; D013237:Stereoisomerism; D014561:Urochordata / Q000737:chemistry
D000470:Alkaloids; D003512:Cyclohexanones; C431548:lepadiformine