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Zhao S , Teijaro C , Chen H , Sirasani G , Vaddypally S , Zdilla M , Dobereiner GE , Andrade RB
Concise Syntheses of Bis-Strychnos Alkaloids (-)-Sungucine, (-)-Isosungucine, and (-)-Strychnogucine B from (-)-Strychnine
Chemistry. 2016 Aug 8;22(33) :11593-6
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We report the first chemical syntheses of complex, bis-Strychnos alkaloids (-)-sungucine (1), (-)-isosungucine (2), and (-)-strychnogucine B (3) from (-)-strychnine (4). Key steps included (1) the Polonovski-Potier activation of strychnine N-oxide; (2) a biomimetic Mannich coupling to forge the signature C23-C5' bond that joins two monoterpene indole monomers; and, (3) a sequential HBr/NaBH3CN-mediated reduction to fashion the ethylidene moieties in 1-3. DFT calculations were employed to rationalize the regiochemical course of reactions involving strychnine congeners.
Zhao, Senzhi Teijaro, Christiana Chen, Heng Sirasani, Gopal Vaddypally, Shivaiah Zdilla, Michael Dobereiner, Graham Andrade, Rodrigo Chemistry. 2016 Jun 15. doi: 10.1002/chem.201602663.