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

• 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
• Journal Title: TETRAHEDRON LETTERS
• Volume: Volume 61, Number 23
• Publisher: PERGAMON-ELSEVIER SCIENCE LTD | 2020-06-04
• Type of Work: Article | Post-print: After Peer Review
• Publisher DOI: http://doi.org/10.1016/j.tetlet.2020.151945
• Subjects: Chemistry, General
• Keywords: Science & Technology; Physical Sciences; Chemistry, Organic; Chemistry; Conjugate addition; Allylstannanes; Oxazolidinone; Pilosinine; Stereodivergent; C'D'E'F'-RING-SYSTEM; CHIROSPECIFIC SYNTHESIS; ASYMMETRIC-SYNTHESIS; BIOLOGICAL-ACTIVITY; FORMAL SYNTHESIS; ACID; PILOCARPINE; MODE

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.