Tetrahedron p. 2041 - 2064 (1991)
Update date:2022-09-26
Topics:
Klusener, P. A. A.
Tip, L.
Brandsma, L.
Isoprene has been metalated in tetrahydrofuran with an excess of sterically hindered potassium dialkylamides, prepared by combining equimolar amounts of the corresponding lithium amide and potassium tert-butoxide.Subsequent reaction with oxirane, alkyl bromides, and pivaldehyde gave the expected coupling products in reasonable yields.Coupling with (CH3)2CHCH2CH=O and (CH3)2C=CHCH=O afforded the bark beetle pheromones (+/-)-ipsenol and (+/-)-ipsdienol in low yields.
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