Total synthesis of (+)-pilosinine via a stereodivergent conjugate addition strategy

TETRAHEDRON LETTERS

卷:61

Article

Schrank, Cassandra L.^1,2  Danneman, Michael W.¹  Prebihalo, Emily A.¹  Anderson, Robert E.¹  Gibson, Tyler J.¹  Wuest, William M.²  Mullins, Richard J.¹ 

[1] Xavier Univ, Dept Chem, 3800 Victory Pkwy, Cincinnati, OH 45207 USA

[2] Emory Univ, Dept Chem, 1515 Dickey Dr, Atlanta, GA 30322 USA

关键词: Conjugate addition;    Allylstannanes;    Oxazolidinone;    Pilosinine;    Stereodivergent;   

DOI  :  10.1016/j.tetlet.2020.151945

来源: Elsevier

【 摘 要 】

In recent work, asymmetric conjugate addition reactions to chiral 4-phenyl-N-enoyl-1,3-oxazolidinones have been shown to give different stereochemical outcomes depending on the conditions employed. Through the application of stereodivergent reaction conditions, the total synthesis of (+)-pilosinine and the formal synthesis of (-)-pilosinine has been completed from a single enantiomer of the 1,3-oxazolidinone auxiliary. (C) 2020 Elsevier Ltd. All rights reserved.

【 授权许可】

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