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

• Type of Material: Article
• Authors: Cassandra L Schrank, Emory University; Michael W Danneman, Xavier University; Emily A Prebihalo, Xavier University; Robert E Anderson, Xavier University; Tyler J Gibson, Xavier University; William Wuest, Emory University; Richard J Mullins, Xavier University
• Language: English
• Date: 2020-06-04
• Publisher: PERGAMON-ELSEVIER SCIENCE LTD
• Publication Version: Author Accepted Manuscript (After Peer Review)
• Copyright Statement: © 2020 Elsevier Ltd. All rights reserved.
• License: Creative Commons Attribution-NonCommercial-NoDerivs 4.0 International
• Final Published Version (URL): http://dx.doi.org/10.1016/j.tetlet.2020.151945
• Title of Journal or Parent Work: TETRAHEDRON LETTERS
• Volume: 61
• Issue: 23
• Grant/Funding Information: This work was funded by the National Institute of General Medical Sciences (R35GM119426 to W.M.W.).
• Keywords: C'D'E'F'-RING-SYSTEM; Pilosinine; BIOLOGICAL-ACTIVITY; ACID; ASYMMETRIC-SYNTHESIS; Conjugate addition; Allylstannanes; PILOCARPINE; Chemistry; CHIROSPECIFIC SYNTHESIS; Stereodivergent; Physical Sciences; FORMAL SYNTHESIS; Chemistry, Organic; Science & Technology; MODE; Oxazolidinone

Abstract

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.