Synthesis of arylnaphthalene lignan scaffold by gold-catalyzed intramolecular sequential electrophilic addition and benzannulation.
An intramolecular approach to generate compounds containing an arylnaphthalene lignan scaffold in high yields is presented. It involves a sequential intramolecular electrophilic attack of carbonyl on arylalkyne followed by benzannulation catalyzed by gold salt. AuCl(3) in combination with AgSbF(6) works better to effect this transformation. Selected products have been converted into arylnaphthalene lactone natural products such as justicidin E, taiwanin C, and retrojusticidin B.
School of Chemistry, University of Hyderabad, Gachibowli, Hyderabad 500046, India.
Vanajakshi
V
Gudla
Rengarajan
R
Balamurugan
D001685:Biological Factors / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D004148:Dioxolanes / Q000737:chemistry; D017612:Gold Compounds / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D001685:Biological Factors; D004148:Dioxolanes; D017612:Gold Compounds; D007783:Lactones; D017705:Lignans; D009281:Naphthalenes; C049719:justicidins; C496008:retrojusticidin B; C467766:taiwanin C; C038016:gold chloride