title: Total synthesis of gracilamine.
abstract: The total synthesis of gracilamine, a pentacyclic Amaryllidaceae alkaloid, was achieved from simple building blocks. The synthesis features a mild photo-Nazarov reaction, intramolecular 1,4-addition, and an intramolecular Mannich reaction. This approach not only confirms the C6 stereochemistry of natural gracilamine, and also provides a novel solution to prepare its derivatives and structurally related natural products.
authors.affiliation: Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663N Zhongshan Road, Shanghai 200062 (China).
authors.forename: Yingbo
authors.initials: Y
authors.lastname: Shi
authors.forename: Baochao
authors.initials: B
authors.lastname: Yang
authors.forename: Shujun
authors.initials: S
authors.lastname: Cai
authors.forename: Shuanhu
authors.initials: S
authors.lastname: Gao
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis*; D001688:Biological Products / Q000737:chemistry; D019668:Liliaceae / Q000737:chemistry*; D008352:Mannich Bases; D008958:Models, Molecular; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D047151:Amaryllidaceae Alkaloids; D001688:Biological Products; D008352:Mannich Bases; C578306:gracilamine
keywords: cross coupling; cyclization; natural products; photochemistry; total synthesis