A Paterno-Büchi approach to the synthesis of merrilactone A.
A six-step approach to the tetracyclic core of merrilactone A is described that uses an intramolecular Paterno-Büchi photoaddition to install the key oxetane ring. Irradiation of bicyclic enone 16, constructed through cyclopentenone alkylation followed by a domino oxy-/carbopalladation reaction, produces the tetracyclic oxetane 17 in excellent yield, having the core carbon skeleton of the target compound merrilactone A. [reaction: see text]
Iriondo-Alberdi
Jone
J
University of Edinburgh, School of Chemistry, Joseph Black Building, King's Buildings, West Mains Road, Edinburgh EH9 3JJ, Scotland, UK.
Perea-Buceta
Jesus E
JE
Greaney
Michael F
MF
D000478:Alkylation; D002384:Catalysis; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry
D007783:Lactones; D012717:Sesquiterpenes; C458341:merrilactone A; D010165:Palladium