title: Total synthesis of (+/-)-pallavicinin and (+/-)-neopallavicinin.
abstract: Through a biomimetic pathway, (+/-)-pallavicinin and (+/-)-neopallavicinin were synthesized from (+/-)-Wieland-Miescher ketone via Grob fragmentation, intramolecular aldol cyclization, and intramolecular Michael reaction. The synthesis was stereocontrolled efficiently and followed the stereochemistry of the Wieland-Miescher ketone, and could provide opportunities for access to analogues of pallavicinin, neopallavicinin, and other related bioactive diterpenoids.
authors: Department of Chemistry, Centre of Novel Functional Molecules, Institute of Chinese Medicine, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, China.
authors: Xiao-Shui
authors: XS
authors: Peng
authors: Henry N C
authors: HN
authors: Wong
mesh_terms: D002942:Circular Dichroism; D004224:Diterpenes / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
chemical_list: D004224:Diterpenes; D006576:Heterocyclic Compounds, 4 or More Rings; C423331:pallavicinin