Synthesis and highly regioselective Diels-Alder reaction of functionalized isoprenes involving a terminal alkoxy group and chemical modification of the resulting …

…, M Kawagishi, M Kawada, J Otera

Index: Mandai, Tadakatsu; Osaka, Kazuhito; Kawagishi, Makoto; Kawada, Mikio; Otera, Junzo Journal of Organic Chemistry, 1984 , vol. 49, # 19 p. 3595 - 3600

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Citation Number: 17

Abstract

A variety of functionalized isoprenes involving a terminal alkoxy group (2 and 3) were newly synthesized according to eq 1, 2, and 3. These compounds proved to undergo a cycloaddition with various unsymmetric dienophiles highly regioselectively without a Lewis acid catalyst. Moreover, the resulting adducts 11 were transformed to cyclohexadienes 12 through elimination of an alcohol.