Total synthesis of (+/-)-hasubanonine.
[reaction: see text] Total synthesis of the alkaloid (+/-)-hasubanonine is described. A key feature of the route is generation of a phenanthrene intermediate via a Suzuki coupling-Wittig olefination-ring-closing metathesis sequence. Conversion of the phenanthrene into the target molecule required six steps including dearomatization by means of oxidative phenolic coupling, anionic oxy-Cope rearrangement, and a final acid-promoted cyclization. Production of an undesired rearranged product in the last step could be suppressed by moderating the acid strength.
Jones
Spencer B
SB
Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602, USA.
He
Liwen
L
Castle
Steven L
SL
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D009020:Morphine / Q000737:chemistry; D010616:Phenanthrenes / Q000138:chemical synthesis* / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry; D031607:Stephania / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D010616:Phenanthrenes; D009020:Morphine; C520169:hasubanonine