Concise and very efficient synthesis of the N-methylwelwistatin tetracyclic core based on an anionic domino process.
An efficient synthesis of the N-methylwelwistatin tetracyclic core in only two steps from Kornfeld's ketone is described, whose key transformation involves the generation of a fused bicyclo[4.3.1]decane ring system through a one-pot sequence comprising a Michael-intramolecular aldolization anionic domino process and a DBU-promoted hydrolysis of the N-pivaloyl protecting group. Besides providing the most efficient synthesis of the welwistatin core to date, this method has the advantage of installing an oxygenated function at the welwistatin D ring.
Ruiz
Miriam
M
Departmento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense.
López-Alvarado
Pilar
P
Menéndez
J Carlos
JC
D000470:Alkaloids / Q000138:chemical synthesis*; D000838:Anions; D001643:Bridged Bicyclo Compounds / Q000737:chemistry; D002384:Catalysis; D006868:Hydrolysis; D026121:Indole Alkaloids; D013696:Temperature
D000470:Alkaloids; D000838:Anions; D001643:Bridged Bicyclo Compounds; D026121:Indole Alkaloids; C092270:welwitindolinone C isothiocyanate