Concise formal synthesis of (+)-pyripyropene A. Issue 29 (19th July 2019)

• Record Type: Journal Article
• Authors: Li, Tao; Wu, Guangmiao; Feng, Shangbiao; Hu, Xiaojun; Zhang, Weiwei; Tang, Shouchu; Xie, Xingang; She, Xuegong
• Is Part Of: Tetrahedron. Volume 75:Issue 29(2019)
• Page Start: 3939
• Page End: 3942
• Publication Date: 2019-07-19
• Subjects: (R)-(−)-Carvone -- [3+2]-Cycloaddition -- (+)-Pyripyropene A -- Formal synthesis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2019.06.017
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A concise enantioselective synthesis of A/B bicyclic segment of naturally occurring α-pyrone meroterpenoid pyripyropene A is achieved in 9 steps (LLS) and 7.5% yield starting from R -(−)-carvone. The significant points of the synthesis include: (1) an intramolecular 1, 3-dipolar cycloaddition reaction to construct the A ring and assemble C4 quaternary carbon stereocenter as well; (2) reductive cleavage of the oxazole motif utilized Raney Ni/B(OCH3 )3 . Graphical abstract: Image 1