The Journal of Organic Chemistry

Anthracyclinones by oxidative dearomatization: total synthesis of SM-173B and aranciamycinone

AS Kende, S Johnson

Index: Kende, Andrew S.; Johnson, Stephen Journal of Organic Chemistry, 1985 , vol. 50, # 5 p. 727 - 729

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Citation Number: 7

Abstract

(11) Isomerization of bicyclo[3.1.0]hex-2-ene to 1,4-cyclohexadiene is exothermic by 11 kcal/mol (Ellis, R. J.; Frey, HM J. Chem. SOC. ... 553). The equilibrium 2a s 4a + 5a lies exclusively to the right (350 "C), AH > 4 kcal/mol. The bridgehead diene system 2a represents a shift of at least 15 kcal/mol in the thermodynamics of the isomerization. Other examples of "wrong-way" homo 1,5-hydrogen shifts have also been noted: (a) Kirsch, R.; Priebe, H.; ...