A Regio‐ and Diastereoselective Stille Coupling/Intramolecular Diels–Alder Cascade for the Generation of Fused Pyridines and Application in the Synthesis of (+)‐Lycopladine A and (−)‐Lycoposerramine R. Issue 42 (19th September 2022)

• Record Type: Journal Article
• Authors: Sim, Kyu‐Hyun; ul Ansari, Thameem; Park, Yong‐Gyu; Jeong, Yeolib; Oh, Sang‐Ha; Min, Hye‐Won; Jeon, Da‐Yoon; Kim, Hyunwoo; Cho, Cheon‐Gyu
• Is Part Of: Angewandte Chemie international edition. Volume 61:Issue 42(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-09-19
• Subjects: Cascade Reactions -- Cycloaddition -- Diels–Alder Reaction -- Stille Cross-Coupling -- Total Synthesis; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.202212016
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: 2‐Pyrones with a chiral branched allylic silyl ether substituent underwent intramolecular Diels–Alder reactions with remarkably high π‐facial‐ and endo‐selectivities. The resulting diastereomerically and enantiomerically pure cycloadducts were transformed into the natural products (+)‐lycopladine A and (−)‐lycoposerramine R. Abstract : Highly efficient asymmetric intramolecular Diels–Alder reactions of 3‐substituted 2‐pyrones were combined with C3‐selective Stille cross‐coupling reactions in a tandem fashion. The resulting diastereomerically and enantiomerically pure cycloadducts were successfully converted into (+)‐lycopladine A and lycoposerramine R.