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

A. Sobolev, M. Vos, H. Zuilhof, F.C.E. Sarabèr, B.J.M. Jansen, Æ. de Groot

Research output: Contribution to journalArticleAcademicpeer-review

6 Citations (Scopus)

Abstract

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
Original languageEnglish
Pages (from-to)29-38
JournalARKIVOC
Volume2005
Issue numberxiv
Publication statusPublished - 2005

Keywords

  • annulation

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