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Stereodivergent Total Syntheses of (+)‐Monomorine I and (+)‐Indolizidine 195B
Author(s) -
Dawood Rafid S.,
Stockman Robert A.
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100453
Subject(s) - chemistry , indolizidine , total synthesis , stereoselectivity , diastereomer , grignard reagent , reagent , enantioselective synthesis , alcohol , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , alkaloid
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.