title: Total synthesis of the Isodon diterpene sculponeatin N.
abstract: The total synthesis of sculponeatin N, a bioactive polycyclic diterpene isolated from Isodon sculponeatus, is reported. Key features of the synthesis include diastereoselective Nazarov and ring-closing metathesis reactions, and a highly efficient formation of the bicyclo[3.2.1]octane ring system by a reductive radical cyclization.
authors: Department of Chemistry, Northwestern University, 2145 Sheridan Rd, Evanston, IL 60208 (USA).
authors: Benjamin J
authors: BJ
authors: Moritz
authors: Daniel J
authors: DJ
authors: Mack
authors: Liuchuan
authors: L
authors: Tong
authors: Regan J
authors: RJ
authors: Thomson
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000737:chemistry; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D056945:Hep G2 Cells; D006801:Humans; D037602:Isodon / Q000737:chemistry* / Q000378:metabolism; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D001643:Bridged Bicyclo Compounds; D004224:Diterpenes; D005609:Free Radicals; D013729:Terpenes; C540959:sculponeatin N
keywords: isodon terpenes; natural products; reductive cyclization; ring-closing metathesis