BF3 x Et2O-mediated cascade cyclizations: synthesis of schweinfurthins F and G.
The total synthesis of the natural stilbene (+)-schweinfurthin G (8) has been accomplished through a sequence based on an efficient cationic cascade cyclization. This cascade process is initiated by Lewis acid promoted ring opening of an epoxide and terminated through a novel reaction with a phenolic oxygen "protected" as its MOM ether. Several Lewis acids have been examined for their ability to induce this new reaction, and BF3 x Et2O was found to be the most effective. The only major byproduct under these conditions was one where the expected secondary alcohol was found as its MOM ether derivative (e.g., 30). While this byproduct could be converted to the original target compound through hydrolysis, it also could be employed as a protected alcohol to allow preparation of a benzylic phosphonate (43) without dehydration of the secondary alcohol. The resulting phosphonate was employed in a Horner-Wadsworth-Emmons condensation with an aldehyde representing the right half of the target compounds, an approach complementary to previous studies based on condensation of a right-half phosphonate and a left-half aldehyde.
Mente
Nolan R
NR
Department of Chemistry, University of Iowa, Iowa City, Iowa 52242-1294, USA.
Neighbors
Jeffrey D
JD
Wiemer
David F
DF
D001880:Boranes / Q000737:chemistry*; D003500:Cyclization; D004986:Ether / Q000737:chemistry*; D013237:Stereoisomerism; D013267:Stilbenes / Q000138:chemical synthesis*
D001880:Boranes; D013267:Stilbenes; C518723:schweinfurthin F; C534360:schweinfurthin G; D004986:Ether; C021274:boron trifluoride
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