639-43-0Relevant articles and documents
Concise total syntheses of (±)-Strychnine and (±)-Akuammicine
Sirasani, Gopal,Paul, Tapas,Dougherty, William,Kassel, Scott,Andrade, Rodrigo B.
, p. 3529 - 3532 (2010)
Concise total syntheses of Strychnos alkaloids strychnine (1) and akuammicine (2) have been realized in 13 and 6 operations, respectively. Key steps include (1) the vinylogous Mannich reaction; (2) a novel, sequential one-pot spirocyclization/intramolecular aza-Baylis-Hillman reaction; and (3) a Heck cyclization. The synthesis of 1 proceeds via the Wieland-Gumlich aldehyde (26).
Syntheses of Strychnos- and Aspidospermatan-Type Alkaloids. 6. Total Syntheses of (+/-)-Echitamidine, (+/-)-Alstogustine, (+/-)-19-epi-Alstogustine, and (+/-)-Akuammicine
Kuehne, Martin E.,Xu, Feng,Brook, Christopher S.
, p. 7803 - 7806 (1994)
19-Oxodihydroakuammicine was obtained in a three-pot sequence, in 25percent overall yield based on a new condensation-sigmatropic rearrangement sequence.Reductions and quaternization reactions furnished the title compounds.
Synthesis of tetracyclic spiroindolines by an interrupted Bischler-Napieralski reaction: total synthesis of akuammicine
Faltracco, Matteo,Ruijter, Eelco
, p. 9641 - 9644 (2021/12/01)
Judicious substrate design allows interruption of the classical Bischler-Napieralski reaction, providing access to a range of diversely substituted tetracyclic spiroindolines. These complex polycyclic scaffolds are valuable building blocks for the construction of indole alkaloids, as showcased in a concise total synthesis of (±)-akuammicine.
Total Synthesis of Strychnine
Lee, Geun Seok,Namkoong, Gil,Park, Jisook,Chen, David Y.-K.
, p. 16189 - 16193 (2017/11/21)
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.