An efficient stereoselective synthesis of penaresidin a from (e)-2-protected amino-3,4-unsaturated sulfoxide.
An efficient, modular, asymmetric synthesis of penaresidin A is disclosed. A beta-protected amino-gamma,delta-unsaturated sulfoxide was prepared by stereoselective addition of the lithio anion of (R)-methyl p-tolyl sulfoxide to an unsaturated sulfinylimine. The pendant sulfoxide group was used as an intramolecular nucleophile to functionalize an alkene regio- and stereoselectively to furnish a bromohydrin, which was employed as the key intermediate in the preparation of the azetidine subunit of penaresidin A. The stereogenic centers of the side chain were introduced by a regioselective opening of an epoxide. Julia-Kocienski olefination was used to couple the azetidine and side chain subunits. The methodology disclosed herein is also useful for the synthesis of ribo- and arabino-phytosphingosines and compounds possessing the amino alcohol moiety.
Raghavan
Sadagopan
S
Organic Division I, Indian Institute of Chemical Technology, Hyderabad 500 007, India. sraghavan@iict.res.in
Krishnaiah
V
V
D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D006573:Heterocyclic Compounds, 1-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013454:Sulfoxides / Q000737:chemistry*
D000473:Alkanes; D000588:Amines; D006573:Heterocyclic Compounds, 1-Ring; D013454:Sulfoxides; C521784:penaresidin