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    Concise Syntheses of bis‐Strychnos Alkaloids (−)‐Sungucine, (−)‐Isosungucine, and (−)‐Strychnogucine B from (−)‐Strychnine

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    Genre
    Post-print
    Date
    2016-06-15
    Author
    Zhao, Senzhi
    Chen, Heng
    Sirasani, Gopal
    Dobereiner, Graham cc
    Andrade, Rodrigo B.
    Teijaro, Christiana cc
    Vaddypally, Shivaiah cc
    Zdilla, Michael cc
    Department
    Chemistry
    Subject
    Sungucine
    Bid-Strychnos alkaloids
    Polonovski-Potier
    Biomimetic synthesis
    Strychnine
    Permanent link to this record
    http://hdl.handle.net/20.500.12613/68
    
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    DOI
    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.
    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
    Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
    Has part
    Chemistry - A European Journal, Vol. 22, Iss. 33
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    ae974a485f413a2113503eed53cd6c53
    http://dx.doi.org/10.34944/dspace/55
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