Concise Syntheses of bis‐Strychnos Alkaloids (−)‐Sungucine, (−)‐Isosungucine, and (−)‐Strychnogucine B from (−)‐Strychnine
Genre
Post-printDate
2016-06-15Author
Zhao, SenzhiChen, Heng
Sirasani, Gopal
Dobereiner, Graham

Andrade, Rodrigo B.
Teijaro, Christiana

Vaddypally, Shivaiah

Zdilla, Michael

Department
ChemistryPermanent link to this record
http://hdl.handle.net/20.500.12613/68
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https://doi.org/10.1002/chem.201602663Abstract
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.Citation
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.Citation to related work
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Chemistry - A European Journal, Vol. 22, Iss. 33ADA compliance
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http://dx.doi.org/10.34944/dspace/55