A versatile synthetic approach to grandisol monoterpene pheromone
A versatile and efficient synthetic procedure for the grandisol pheromone library has been established. The key feature of our synthesis involves a versatile and highly regioselective Pd(0)-catalyzed intramolecular allylic alkylation for the key cyclobutane skeleton of grandisol. In this connection, the concise synthesis of (±)-grandisol as well as mechanism study of Pd(0)-catalyzed regioselective cyclization as a key reaction have also been accomplished.
Han, Young Taek,Kim, Nam-Jung,Jung, Jong-Wha,Yun, Hwayoung,Lee, Sujin,Suh, Young-Ger
experimental part
p. 1437 - 1442
(2012/04/23)
Pheromone Synthesis, CXXXVII. A New Synthesis of (+)-Grandisol
The natural and (+)-enantiomer of grandisol has been synthesized from (R)-(-)-carvone (2) by employing the intramolecular alkylation of 8 to give 9 as the key step. Key words: Anthonomus grandis; oll weevil; carvone; grandisol; pheromones
Mori, Kenji,Fukamatsu, Kunio
p. 489 - 494
(2007/10/02)
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