A Pauson-Khand approach to the hamigerans.
An intramolecular Pauson-Khand reaction has been used in the construction of the tricyclic core common to the hamigeran terpenes. For effective cyclization, it was necessary to tether the olefin-containing moiety to the aromatic framework to reduce its conformation mobility; this was accomplished using a silylene protecting group. Efficient construction of the aryl enyne from a salicylic acid derivative was accomplished via ortho lithiation and Sonogashira cross-coupling chemistry.
Madu
Christian E
CE
Department of Chemistry and Biochemistry, The University of Texas at Arlington, Arlington, TX 76019, USA.
Lovely
Carl J
CJ
D001688:Biological Products / Q000737:chemistry; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry
D001688:Biological Products; D009285:Naphthoquinones