55304-03-5Relevant articles and documents
Synthesis of phytuberin. 4-endo-tet acid-catalyzed cyclization of α-hydroxy epoxides
Prange, Thierry,Rodriguez, Maria S.,Suarez, Ernesto
, p. 4422 - 4431 (2007/10/03)
The total synthesis of phytuberin, a phytoalexin of the Solanum genus, from (-)-α-santonin is reported. The key steps include (a) reductive cleavage of the C-O bond of the γ-lactone with concomitant protection of the C1 double bond, (b) Sharpless stereocontrolled hydroxy-assisted epoxidation of allylic alcohol 6 and simultaneous deprotection of the C1 double bond, (c) a rare 4-endo-tet acid-catalyzed cyclization of an α-hydroxy epoxide, and (d) an unprecedented 4-exo selenocyclization of a homoallylic alcohol.
A Convenient, Stereospecific Synthesis of (-)-Phytuberin from (-)-2-Carone
Caine, Drury,Smith, Troy L. Jr.
, p. 7568 - 7570 (2007/10/02)
-