A Concise Route to the Strongylophorines. (30th May 2016)

• Record Type: Journal Article
• Authors: Yu, Wanwan; Hjerrild, Per; Overgaard, Jacob; Poulsen, Thomas B.
• Is Part Of: Angewandte Chemie. Volume 128:Number 29(2016)
• Page Start: 8434
• Page End: 8438
• Publication Date: 2016-05-30
• Subjects: C-H-Aktivierung -- Cyclisierungen -- Naturstoffe -- Reaktionskaskaden -- Semisynthese; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201602476
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: An efficient eight‐step semisynthesis of strongylophorine‐2 from the abundant building block isocupressic acid is reported. The route represents the first synthetic entry into this class of natural products and provides access to six additional family members. A novel iron(III)‐mediated rearrangement–cyclization cascade and a directed photochemical sp 3 C−H δ ‐lactonization are the key transformations that enable concise assembly of these bioactive polycyclic meroterpenoids.