Annelations of cyclic Beta-cyanoketones in the synthesis of functionalized polycyclic compounds and steroids

Cyclic ß-cyano ketones like cyanocarvone and 3-cyano-2-methylcyclopentanone can be annelated in high yields with methyl vinyl ketone, ethyl vinyl ketone and 6(3- methoxyphenyl)hex-1-en-3-one to cyano-substituted decalones and indanones. Computational studies at the B3LYP/6-31+G(d,p)//B3LYP/6-31G(d,p...

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Published inARKIVOC free online journal of organic chemistry Vol. 2005
Main Authors Sobolev, A, Vos, M, Zuilhof, H, Sarabèr, F.C.E, Jansen, B.J.M, Groot, Æ., de
Format Journal Article
Published 2005
Subjects
annulation
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Summary:Cyclic ß-cyano ketones like cyanocarvone and 3-cyano-2-methylcyclopentanone can be annelated in high yields with methyl vinyl ketone, ethyl vinyl ketone and 6(3- methoxyphenyl)hex-1-en-3-one to cyano-substituted decalones and indanones. Computational studies at the B3LYP/6-31+G(d,p)//B3LYP/6-31G(d,p) level of theory show that thermodynamic rather than kinetic factors can explain the high yields. The annelated products are suitable intermediates for the synthesis of isoprenoid, steroid and homo steroid skeletons
ISSN:1551-7004
1551-7012
DOI:10.3998/ark.5550190.0006.e04