Total synthesis of (+)-aspidospermidine: a new strategy for the enantiospecific synthesis of aspidosperma alkaloids.
A new strategy was developed for the enantiospecific synthesis of aspidosperma alkaloids. The key steps involve a novel ketene-lactonization reaction of a chiral vinyl sulfoxide to efficiently set up the quaternary carbon center, and a tandem Michael addition-alkylation reaction sequence to form the polycyclic core structure. This new strategy was employed in the total synthesis of natural product (+)-aspidospermidine.
Marino
Joseph P
JP
Department of Chemistry, The University of Michigan, Ann Arbor 48109, USA. jpmarino@nd.edu
Rubio
Maria B
MB
Cao
Ganfeng
G
de Dios
Alfonso
A
D000470:Alkaloids / Q000138:chemical synthesis*; D030009:Aspidosperma / Q000737:chemistry; D026121:Indole Alkaloids; D007211:Indoles; D011804:Quinolines; D013237:Stereoisomerism
D000470:Alkaloids; D026121:Indole Alkaloids; D007211:Indoles; D011804:Quinolines; C409672:aspidospermidine