Stereodivergent total syntheses of precoccinelline, hippodamine, coccinelline, and convergine.
[structure: see text] A stereodivergent approach toward total syntheses of Coccinellidae defensive alkaloids is described. These syntheses feature a highly diastereoselective intramolecular aza-[3 + 3] annulation strategy, which represents a de novo approach to this family of natural products.
Gerasyuto
Aleksey I
AI
Division of Pharmaceutical Sciences and Department of Chemistry, Rennebohm Hall, 777 Highland Avenue, University of Wisconsin, Madison, Wisconsin 53705, USA.
Hsung
Richard P
RP
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D001517:Coleoptera / Q000737:chemistry; D003497:Cyclic N-Oxides / Q000138:chemical synthesis* / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011799:Quinazolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D003497:Cyclic N-Oxides; D006575:Heterocyclic Compounds, 3-Ring; D011799:Quinazolines; C520394:convergine; C511678:hippodamine; C467904:coccinelline