An improved synthesis of pennogenin. Issue 12 (22nd March 2019)

• Record Type: Journal Article
• Authors: Gao, Ran; Shi, Yong; Tian, Wei-Sheng
• Is Part Of: Tetrahedron. Volume 75:Issue 12(2019)
• Page Start: 1717
• Page End: 1721
• Publication Date: 2019-03-22
• Subjects: Pennogenin -- Chonglou -- Diosgenin -- Diboration/oxidation -- C17α-OH steroid; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.11.009
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: An improved synthesis of pennogenin, a bioactive component of Chinese herb "Chonglou" ( Paris ), is described. A ring-switching process opened the ring E of diosgenin and allowed the use of a hydroxyl-directed diboration/oxidation to introduce C17α-OH, hence eliminating the use of OsO4 . This strategy might be rendered to synthesize similar steroids with C17α-OH. Graphical abstract: Image 1