Total synthesis of the neotropical poison-frog alkaloid (-)-205B.
[reaction: see text]. A stereocontrolled total synthesis of the neotropical poison-frog alkaloid (-)-205B (1) has been achieved, employing a dithiane three-component linchpin coupling, a one-pot sequential construction of the embedded indolizidine ring, and ring-closing metathesis (RCM) to arrive at the novel 8b-azaacenaphthylene ring system comprising the alkaloid. The synthesis proceeded with a longest linear sequence of 19 steps, affording (-)-1 in 5.6% overall yield.
Smith
Amos B
AB
Department of Chemistry, University of Pennsylvania, Philadelphia, 19104, USA. smithab@sas.upenn.edu
Kim
Dae-Shik
DS
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D001001:Anura; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000470:Alkaloids; D006575:Heterocyclic Compounds, 3-Ring; C510161:alkaloid (-)-205B