Biomimetic Total Syntheses of (−)‐Leucoridines A and C through the Dimerization of (−)‐Dihydrovalparicine | Zendy

Kokkonda Praveen | Zendy; Brown Keaon R. | Zendy; Seguin Trevor J. | Zendy; Wheeler Steven E. | Zendy; Vaddypally Shivaiah | Zendy; Zdilla Michael J. | Zendy; Andrade Rodrigo B. | Zendy

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Biomimetic Total Syntheses of (−)‐Leucoridines A and C through the Dimerization of (−)‐Dihydrovalparicine

Author(s) -

Kokkonda Praveen,

Brown Keaon R.,

Seguin Trevor J.,

Wheeler Steven E.,

Vaddypally Shivaiah,

Zdilla Michael J.,

Andrade Rodrigo B.

Publication year - 2015

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201505198

Subject(s) - strychnos , biomimetic synthesis , cycloaddition , indole test , chemistry , stereochemistry , sequence (biology) , total synthesis , alkaloid , combinatorial chemistry , organic chemistry , catalysis , biochemistry

Concise biomimetic syntheses of the Strychnos‐Strychnos‐type bis‐indole alkaloids (−)‐leucoridine A ( 1 ) and C ( 2 ) were accomplished through the biomimetic dimerization of (−)‐dihydrovalparicine ( 3 ). En route to 3 , the known alkaloids (+)‐geissoschizoline ( 8 ) and (−)‐dehydrogeissoschizoline ( 10 ) 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.

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