Tetrahedron

Biomimetic heterocyclisation of aryl olefins one-step formation of two carbon-carbon bonds

J Dijkink, WN Speckamp

Index: Dijkink,J.; Speckamp,W.N. Tetrahedron, 1978 , vol. 34, p. 173 - 178

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Citation Number: 40

Abstract

Cyclisation of ethoxylactam 5 in formic acid at room temperature gives rise to stereospecific formation of 9. Similar reaction of the olefin 6 possessing unnatural geometry also proceeds stereospecific and in quantitative yield to the tetracyclic product 10. The acetylene 7 equally affords 11. Upon Me-substitution of the olefinic double bond the cyclisation of 8 has to be carried out in trifluoroacetic acid-dichloromethane in order to obtain a 84% yield of 12 ...