Journal of the American Chemical Society

Model studies of terpene biosynthesis. Intermolecular 1'-2 electrophilic condensation of 3-methyl-2-butenyl acetate

CHR King, CD Poulter

文献索引：King, Chi-Hsin R.; Poulter, C. Dale Journal of the American Chemical Society, 1982 , vol. 104, # 5 p. 1413 - 1420

全文：HTML全文

被引用次数: 11

摘要

Abstract: The stereochemistry of the carbon-carbon bond-forming step in the electrophilic intermolecular 1'-2 condensation of 3-methyl-2-butenyl acetate (I-OAc) to yield lavandulyl acetate (2-OAc) was studied. Treatment of (lS)-[1-2H] 3-methyl-2-butenyl acetate ((lS)-[l-'H] 1- OAc) with aluminum trichloride in ethyl acetate gave labeled lavandulyl acetate ([1, 3-'H2] 2- OAc)(30%) and isoprene (65%) as the major products. The configurations at C (1), C (2), ...