Biomimetic Total Syntheses of (−)‐Leucoridines A and C through the Dimerization of (−)‐Dihydrovalparicine. (10th September 2015)

• Record Type: Journal Article
• Authors: Kokkonda, Praveen; Brown, Keaon R.; Seguin, Trevor J.; Wheeler, Steven E.; Vaddypally, Shivaiah; Zdilla, Michael J.; Andrade, Rodrigo B.
• Is Part Of: Angewandte Chemie. Volume 127:Number 43(2015)
• Page Start: 12823
• Page End: 12826
• Publication Date: 2015-09-10
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201505198
• Languages: English
• ISSNs: 0044-8249

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Concise biomimetic syntheses of the Strychnos‐Strychnos‐type bis‐indole alkaloids (−)‐leucoridine A (<bold>1</bold>) and C (<bold>2</bold>) were accomplished through the biomimetic dimerization of (−)‐dihydrovalparicine (<bold>3</bold>). En route to <bold>3</bold>, the known alkaloids (+)‐geissoschizoline (<bold>8</bold>) and (−)‐dehydrogeissoschizoline (<bold>10</bold>) were also prepared. DFT calculations were employed to elucidate the mechanism, which favors a stepwise aza‐Michael/spirocyclization sequence over the alternate hetero‐Diels–Alder cycloaddition reaction.</p> </abstract>