Total synthesis of (+)-demethoxycardinalin 3.
The total synthesis of (+)-demethoxycardinalin 3 is described. The synthetic strategy features the synthesis of dimeric Fischer carbene and its use in a bidirectional Dötz benzannulation reaction to set the dimeric structure of the cardinalins. The oxa-Pictet-Spengler reaction was used to construct the pyran rings. The synthesis is completed in seven steps and an overall yield of 7%.
Fernandes
Rodney A
RA
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, Maharashtra, India. rfernand@chem.iitb.ac.in
Mulay
Sandip V
SV
D016227:Benzoquinones / Q000138:chemical synthesis* / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D016227:Benzoquinones; C555284:demethoxycardinalin 3; C030011:carbene; D008697:Methane