Organotellurides as a source of organometallics: application in the synthesis of (+/−)-frontalin

A concise enantioselective synthesis of (+)-endo-brevicomin accomplished by a tellurium/metal exchange reaction

“…The resulting organolithium was converted into the higher order cyanocuprate in the usual way, and then reacted with 2. 5,6,9 The hydroxy-ketal originated from this reaction was directly treated with hydrochloric acid or p-TSA resulting in the racemic mixture of (+/-)-(endo/exo)-brevicomin (1) in 70% isolated yield.…”

“…2 Complementary to these methodologies, is the tellurium/ lithium exchange reaction. 3 Previously we demonstrated the synthetic application and efficacy of the tellurium/ lithium exchange reaction to generate functionalized organolithium reagents 4 as well as to prepare other classes of organometallics, including organomagnesium, 5 organocoper, [5][6][7] and organocerium 7 reactive reagents. Herein, we report the enantioselective synthesis of the pine beetle pheromone (+)-endo-brevicomin 8 (1) and its racemic mixture using a telluride as the key precursor of a functionalized organometallic reagent.…”

Antioxidant effect of functionalized alkyl-organotellurides: a studyin vitro

“…Tellurides B and C were prepared in good yields according to our previous protocols [27][28][29][30][31] from telluride A. Finally, telluride D was prepared (65% isolated yield) from compound A by reacting with hydroxylamine hydrochloride 32 .…”

Insect pheromone synthesis in Brazil: an overview

“…Through unambiguous syntheses of both enantiomers and biological testing, Mori 133,134 has shown that the absolute configuration of the biologically active compound is (1S,5R)-40. dos Santos et al 135 described the synthesis of (±)-frontalin (40) in 65% overall yield, employing an organocuprate generated by tellurium/lithium exchange in the key step (Scheme 41). …”