Total synthesis of chiral biaryl natural products by asymmetric biaryl coupling.
This tutorial review highlights the use of catalytic asymmetric 2-naphthol couplings in total synthesis. The types of chirality, chiral biaryl natural products, prior approaches to chiral biaryl natural products, and other catalytic asymmetric biaryl couplings are outlined. The three main categories of chiral catalysts for 2-naphthol coupling (Cu, V, Fe) are described with discussion of their limitations and advantages. Applications of the copper catalyzed couplings in biomimetic syntheses are discussed including nigerone, hypocrellin, calphostin D, phleichrome, and cercosporin.
Department of Chemistry, Roy and Diana Vagelos Laboratoies, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA. marisa@sas.upenn.edu
Marisa C
MC
Kozlowski
Barbara J
BJ
Morgan
Elizabeth C
EC
Linton
D001688:Biological Products / Q000138:chemical synthesis*; D002384:Catalysis; D019216:Metals, Heavy / Q000737:chemistry; D009284:Naphthols / Q000737:chemistry; D011084:Polycyclic Aromatic Hydrocarbons / Q000737:chemistry*; D013237:Stereoisomerism
D001688:Biological Products; D019216:Metals, Heavy; D009284:Naphthols; D011084:Polycyclic Aromatic Hydrocarbons; C028405:2-naphthol