Total Synthesis of Strychnine

The total synthesis of the flagship Strychnos indole alkaloid, strychnine, has been accomplished. The developed synthetic sequence features a novel vinylogous 1,4‐addition, a challenging iodinium salt mediated silyl enol ether arylation, a palladium‐catalyzed Heck reaction, and a streamlined late‐st...

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Bibliographic Details
Published in:Chemistry : a European journal 2017-11, Vol.23 (64), p.16189-16193
Main Authors: Lee, Geun Seok, Namkoong, Gil, Park, Jisook, Chen, David Y.‐K.
Format: Article
Language:English
Subjects:
Alkaloids - chemical synthesis
Alkaloids - chemistry
arylation reactions
Catalysis
Chemical synthesis
Chemistry
Indoles
Indoles - chemistry
natural products
Optical activity
Palladium
Palladium - chemistry
Salts
Stereoisomerism
Strychnine
Strychnine - chemical synthesis
Strychnine - chemistry
Strychnos toxifera
total synthesis
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Summary:The total synthesis of the flagship Strychnos indole alkaloid, strychnine, has been accomplished. The developed synthetic sequence features a novel vinylogous 1,4‐addition, a challenging iodinium salt mediated silyl enol ether arylation, a palladium‐catalyzed Heck reaction, and a streamlined late‐stage conversion to strychnine. Furthermore, an application of asymmetric counterion‐directed catalysis (ACDC) in the context of target‐oriented organic synthesis has been rendered access to an optically active material. The synthetic sequence described herein represents the most concise entry to optically active strychnine to date. What′s your poison? An expedient total synthesis of strychnine has been accomplished through a newly developed reaction sequence involving a catalytic asymmetric counteranion‐directed vinylogous 1,4‐addition, a silyl enol ether quaternary arylation, and an intramolecular Heck reaction.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201704455