4.5 Article

Stereodivergent Total Syntheses of (+)-Monomorine I and (+)-Indolizidine 195B

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2021, Issue 27, Pages 3850-3853

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202100453

Keywords

Chiral auxiliary; Natural Product; Pyrrolidine; Stereodivergent; Sulfinimine

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This method efficiently synthesizes two natural products (+)-monomorine I and (+)-indolizidine 195B in high yields from a readily available alcohol, with selective access to two distinct diastereomers through the judicious use of solvent in a nucleophilic addition reaction.
A simple and efficient stereoselective total syntheses of two natural products (+)-monomorine I and (+)-indolizidine 195B in high yields starting from a readily available alcohol is described. The key step in this synthetic route exploits the judicious use of solvent to enable a closed or open transition state in a nucleophilic addition of Grignard reagent to sulfinimine, giving selective access to two distinct diastereomers required for the formation of the two target natural products.

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