The analysis of two distinct strategies toward the enantioselective formal total synthesis of (+)-Gelsenicine

A full account of a formal enantioselective total synthesis of (+)-gelsenicine is described. Separate strategies based on catalytic cycloisomerization as the central step are considered. One plan involves chirality transfer from enantioenriched substrates, while the other employs asymmetric catalysi...

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Bibliographic Details
Published in:Tetrahedron 2023-03, Vol.134, p.133278, Article 133278
Main Authors: Ji, Haofan, Knutson, Phil C., Harrington, Christopher M., Ke, Yan-Ting, Ferreira, Eric M.
Format: Article
Language:English
Subjects:
Alkyne activation
Asymmetric catalysis
Chirality transfer
Gelsenicine
Gold
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Summary:A full account of a formal enantioselective total synthesis of (+)-gelsenicine is described. Separate strategies based on catalytic cycloisomerization as the central step are considered. One plan involves chirality transfer from enantioenriched substrates, while the other employs asymmetric catalysis. The chirality transfer strategy is less effective, while in the latter, phosphoramidite- and bisphosphine-gold complexes are tested and ultimately provide a key intermediate in high enantiopurity in our Gelsemium alkaloid syntheses. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2023.133278