Asymmetric Synthesis of Trifluoromethylated ent‐Fragransin C1. Issue 12 (21st January 2019)

• Record Type: Journal Article
• Authors: Racochote, Sasirome; Pohmakotr, Manat; Kuhakarn, Chutima; Leowanawat, Pawaret; Reutrakul, Vichai; Soorukram, Darunee
• Is Part Of: European journal of organic chemistry. Issue 12(2019)
• Page Start: 2212
• Page End: 2223
• Publication Date: 2019-01-21
• Subjects: Asymmetric synthesis -- Lignans -- Fluorine -- Natural products; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201801676
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Asymmetric synthesis of trifluoromethylated derivative of ent ‐fragransin C1 was reported. The installation of contiguous stereochemistries across the tetrahydrofuran scaffold was achieved through stereocontrolled conjugate addition, aldol reaction, and a protection‐free intramolecular C‐O bond formation (furan ring formation) via chemoselective generation of the benzylic carbocation. Abstract : Asymmetric synthesis of trifluoromethylated ent ‐fragransin C1 bearing a chiral trifluoromethyl motif was achieved with high stereoselectivity. The key synthetic strategies involved stereocontrolled conjugate addition, aldol reaction, and a protection‐free furan ring formation via chemoselective generation of the benzylic carbocation from enantioenriched 1, 4‐diarylbutanetriol derivative.