Total syntheses of 2,2'-epi-cytoskyrin A, rugulosin, and the alleged structure of rugulin.
The total syntheses of 2,2'-epi-cytoskyrin A, rugulosin, and the alleged structure of rugulin are described. These naturally occurring bisanthraquinones and their relatives are characterized by novel molecular architectures at the core, at which lies a more or less complete, cage-like structural motif termed "skyrane". The strategies developed for their total synthesis feature a cascade sequence called the "cytoskyrin cascade" and deliver these molecules in short order and in a stereoselective manner.
Nicolaou
K C
KC
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA. kcn@scripps.edu
Lim
Yee Hwee
YH
Piper
Jared L
JL
Papageorgiou
Charles D
CD
D000880:Anthraquinones / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D019281:Dimerization; D005609:Free Radicals / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D009285:Naphthoquinones / Q000737:chemistry*; D009570:Nitriles / Q000737:chemistry; D010084:Oxidation-Reduction
D000880:Anthraquinones; D005609:Free Radicals; D009285:Naphthoquinones; D009570:Nitriles; C419462:cytoskyrin A; C029548:rugulosin; C015829:rugulin