Diastereoselective synthesis of the pectenotoxin 2 non-anomeric AB spiroacetal.
The reductive cyclization reaction of a cyanoacetal has been used to prepare the pectenotoxin 2 (PTX-2) AB spiroacetal with high diastereoselectively for the first time. The strategy is convergent and makes use of the axial-selective reductive lithiation of 2-cyano tetrahydropyran rings to introduce the spiroacetal center with the desired non-anomeric selectivity. [reaction: see text].
Vellucci
Danielle
D
Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, Irvine, California, 92697-2025, USA.
Rychnovsky
Scott D
SD
D000818:Animals; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis*; D018942:Macrolides; D009682:Magnetic Resonance Spectroscopy; D008387:Marine Toxins / Q000138:chemical synthesis*; D049897:Pectinidae; D011714:Pyrans / Q000138:chemical synthesis*; D013237:Stereoisomerism; D000095702:Polyether Toxins
D005663:Furans; D018942:Macrolides; D008387:Marine Toxins; D011714:Pyrans; C098380:pectenotoxin 2; D000095702:Polyether Toxins