The Journal of Organic Chemistry

Diels-Alder reactions of. beta.-stannyl enones. Synthesis of. DELTA. 3-carene, isosesquicarene, and other bicyclo [4.1. 0] hept-3-enes

CR Johnson, JF Kadow

Index: Johnson, Carl R.; Kadow, John F. Journal of Organic Chemistry, 1987 , vol. 52, # 8 p. 1493 - 1500

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Citation Number: 52

Abstract

Various trans-8-stannyl enones, trans-3-(tributylstannyl)-2-propenal, and trans-ethyl 3- (tributylstannyl)-2-propenoate were prepared and found to readily undergo Diels-Alder reactions with 1, 3-dienes. The cycloaddition occurs with maintenance of trans tin/carbonyl stereochemistry to give high yields of adducts. The carbonyl moieties of the cycloadducts were converted to alcohols or epoxides which are subsequently transformed into bicyclo-[ ...