The Organoalkali Route to Vitamin A and β??Carotene

G Rauchschwalbe, A Zellner…

Index: Rauchschwalbe, Guenter; Zellner, Armin; Schlosser, Manfred European Journal of Organic Chemistry, 2001 , # 20 p. 3903 - 3909

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Citation Number: 4

Abstract

Abstract The reductive cleavage of methyl vinyl-β-ionyl ether (1) or the deprotonation of 3, 2′, 6′, 6′-tetramethyl-5-(1-cyclohexenyl)-1, 3-pentadiene (2) gives rise to an organometallic C 15 species that combines selectively with a variety of electrophiles at the terminal chain position. Its reaction with aldehydes, however, is less clean. In particular,(E)-β- formyl-2-butenyl acetate gives the expected adduct 7a and, after dehydration, vitamin A ...