title: A 7-Step Formal Asymmetric Total Synthesis of Strictamine via an Asymmetric Propargylation and Metal-Mediated Cyclization.
abstract: Herein is shown how a novel catalytic asymmetric propargylation of 3,4-dihydro-β-carboline, followed by a designed Au(I)/Ag(I)-mediated 6-endo-dig cyclization, can directly deliver the indolenine-fused methanoquinolizidine core of the akuammiline alkaloid strictamine in its native oxidation state, ultimately achieving a 7-step formal asymmetric total synthesis. Also demonstrated are how the cyclization products can rearrange into vincorine-type skeletons and a further use for the developed propargylation with the first catalytic asymmetric total synthesis of decarbomethoxydihydrogambirtannine.
authors.affiliation: Columbia University , Dept. of Chemistry, 3000 Broadway, New York, New York 10027, United States.|The Scripps Research Institute , Dept. of Chemistry, 130 Scripps Way, Jupiter, Florida 33458, United States.
authors.forename: Myles W
authors.identifier: 0000-0002-0231-0059
authors.initials: MW
authors.lastname: Smith
authors.affiliation: University of Chicago , Dept. of Chemistry, 5735 S. Ellis Avenue, Chicago, Illinois 60637, United States.
authors.forename: Zhiyao
authors.initials: Z
authors.lastname: Zhou
authors.affiliation: The Scripps Research Institute , Dept. of Chemistry, 130 Scripps Way, Jupiter, Florida 33458, United States.
authors.forename: Alison X
authors.initials: AX
authors.lastname: Gao
authors.affiliation: University of Chicago , Dept. of Chemistry, 5735 S. Ellis Avenue, Chicago, Illinois 60637, United States.
authors.forename: Takuya
authors.initials: T
authors.lastname: Shimbayashi
authors.affiliation: Columbia University , Dept. of Chemistry, 3000 Broadway, New York, New York 10027, United States.|The Scripps Research Institute , Dept. of Chemistry, 130 Scripps Way, Jupiter, Florida 33458, United States.|University of Chicago , Dept. of Chemistry, 5735 S. Ellis Avenue, Chicago, Illinois 60637, United States.
authors.forename: Scott A
authors.identifier: 0000-0003-3594-8769
authors.initials: SA
authors.lastname: Snyder