Silicon-directed nazarov cyclizations VII. Linearly-fused tricyclics

Scott E. Denmark, Russell C. Klix

Research output: Contribution to journalArticlepeer-review


A new modification of the silicon-directed Nazarov cyclization is described which involves the cyclization of divinyl ketones incorporating an allylsilane as the control unit. The cyclizations are extremely facile with FeCl3 or BF3·OEt2 as the Lewis acid. Four permutations of five- and six-membered ring substrates have been examined. In all cases the reactions are regio- and stereoslective. In the 6-5-6 (6ba) and 5-5-6 (6ba) systems the major product has the trans-anti configuration. The ability to incorporate a methyl substituent on the double bond and in the ring has been addressed.

Original languageEnglish (US)
Pages (from-to)4043-4060
Number of pages18
Issue number13
StatePublished - 1988

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry


Dive into the research topics of 'Silicon-directed nazarov cyclizations VII. Linearly-fused tricyclics'. Together they form a unique fingerprint.

Cite this