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Concise Syntheses of bis‐Strychnos Alkaloids (−)‐Sungucine, (−)‐Isosungucine, and (−)‐Strychnogucine B from (−)‐Strychnine
Zhao, Senzhi Chen, Heng Sirasani, Gopal Andrade, Rodrigo B.
Zhao, Senzhi
Chen, Heng
Sirasani, Gopal
Andrade, Rodrigo B.
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Post-print
Date
2016-06-15
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Chemistry
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https://doi.org/10.1002/chem.201602663
Abstract
The first chemical syntheses of complex, bis‐Strychnos alkaloids (−)‐sungucine (1), (−)‐isosungucine (2), and (−)‐strychnogucine B (3) from (−)‐strychnine (4) is reported. 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.
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Zhao, Senzhi; Teijaro, Christiana N.; Chen, Heng; Sirasani, Gopal; Vaddypally, Shivaiah; Zdilla, Michael J.; Dobereiner, Graham E.; Andrade, Rodrigo B. (2016): Concise Syntheses of bis‐Strychnos Alkaloids (−)‐Sungucine, (−)‐Isosungucine, and (−)‐Strychnogucine B from (−)‐Strychnine. Postprint. 10.1002/chem.201602663.
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Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
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Chemistry - A European Journal, Vol. 22, Iss. 33
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