One-pot multiple reactions: asymmetric synthesis of 2, 6-cis-disubstituted piperidine alkaloids from chiral aziridine. Issue 27 (18th May 2016)

• Record Type: Journal Article
• Authors: Yadav, Nagendra Nath; Choi, Jihye; Ha, Hyun-Joon
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 27(2016)
• Page Start: 6426
• Page End: 6434
• Publication Date: 2016-05-18
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob00806b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : 2, 6- cis -Disubstituted piperidine alkaloids were synthesized from chiral aziridines through one-pot multiple reactions. Abstract : A divergent, new, and highly stereoselective synthesis of cis -2, 6-disubstituted piperidine natural products including isosolenopsins, deoxocassine, and spectaline was achieved from chiral aziridine decorated with appropriate alkyl chains for isosolenopsins or alkynyl groups for deoxocassine and spectaline at C2. The characteristic feature of this synthesis is one-pot sequential reactions under atmospheric hydrogen including the reduction of alkyne (for deoxocassine and spectaline), reductive ring-opening of aziridine, debenzylation, and intramolecular reductive amination in high yields. The prerequisite aziridines were elaborated from commercially available (2 S )-hydroxymethylaziridine through oxidation, Wittig olefination, and the Grignard reaction for isosolenopsins or substrate-controlled lithium alkynylate addition for deoxocassine and spectaline.