Total synthesis of (+/-)-pallavicinin and (+/-)-neopallavicinin.
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.
Peng
Xiao-Shui
XS
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.
Wong
Henry N C
HN
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
D004224:Diterpenes; D006576:Heterocyclic Compounds, 4 or More Rings; C423331:pallavicinin