Concise total syntheses of (+/-)-strychnine and (+/-)-akuammicine.
Concise total syntheses of Strychnos alkaloids strychnine (1) and akuammicine (2) have been realized in 13 and 6 operations, respectively. Key steps include (1) the vinylogous Mannich reaction; (2) a novel, sequential one-pot spirocyclization/intramolecular aza-Baylis-Hillman reaction; and (3) a Heck cyclization. The synthesis of 1 proceeds via the Wieland-Gumlich aldehyde (26).
Sirasani
Gopal
G
Department of Chemistry, Temple University Philadelphia, Pennsylvania 19122, USA.
Paul
Tapas
T
Dougherty
William
W
Kassel
Scott
S
Andrade
Rodrigo B
RB
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D013331:Strychnine / Q000138:chemical synthesis* / Q000737:chemistry
D000470:Alkaloids; D007211:Indoles; D013331:Strychnine; C434103:akuammicine