Premium
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.