Total synthesis of (+)-pilosinine via a stereodivergent conjugate addition strategy. Issue 23 (4th June 2020)

• Record Type: Journal Article
• Authors: Schrank, Cassandra L.; Danneman, Michael W.; Prebihalo, Emily A.; Anderson, Robert E.; Gibson, Tyler J.; Wuest, William M.; Mullins, Richard J.
• Is Part Of: Tetrahedron letters. Volume 61:Issue 23(2020)
• Publication Date: 2020-06-04
• Subjects: Conjugate addition -- Allylstannanes -- Oxazolidinone -- Pilosinine -- Stereodivergent; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2020.151945
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Chiral auxiliary controlled 1, 4-conjugate addition of an allylstannane. Chiral auxiliary controlled 1, 4-conjugate addition of an allyl organocopper reagent. Divergent stereochemical outcomes from the same chiral auxiliary. Synthesis of (+)-pilosinine in 7 steps (26% overall yield). 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.