Copper‐Catalyzed Synthesis of a Highly Hydroxy‐Functionalized Benzo[e]indolizidine by Intramolecular N‐Arylation1. Issue 22 (17th June 2013)

• Record Type: Journal Article
• Authors: Cordero, Franca M.; Khairnar, Bhushan B.; Bonanno, Paola; Martinelli, Andrea; Brandi, Alberto
• Is Part Of: European journal of organic chemistry. Issue 22(2013)
• Page Start: 4879
• Page End: 4886
• Publication Date: 2013-06-17
• Subjects: Azasugars -- Fused‐ring systems -- Copper catalysis -- Cross‐coupling -- Cycloaddition; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201300440
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: The enantiopure (2 S, 3 S, 3a S, 5 S )‐1, 2, 3, 3a, 4, 5‐hexahydropyrrolo[1, 2‐ a ]quinoline‐2, 3, 5‐triol (2, 3, 5‐trihydroxybenzo[ e ]indolizidine) framework has been synthesized by a straightforward strategy consisting of 1, 3‐dipolar cycloaddition of a pyrroline N ‐oxide to 2‐bromostyrene followed by isoxazolidine N–O bond reduction and cyclization by copper‐catalyzed nucleophilic aromatic substitution of the intermediate pyrrolidine. Abstract : Highly hydroxy‐functionalized hexahydropyrrolo[1, 2‐ a ]quinolines that have the same absolute configuration at stereocenters C‐2, C‐3 and C‐3a as natural lentiginosine have been synthesized through a three‐step sequence starting from enantiopure dialkoxypyrroline N ‐oxides derived fromL ‐tartaric acid.