Nitro compounds in the double annulation route to trans-fused bicyclic compounds

Robert B. Grossman, Ravindra M. Rasne, Brian O. Patrick

Research output: Contribution to journalArticlepeer-review

17 Scopus citations


Tethered carbon acids bearing nitro groups undergo a double Michael reaction with 3-butyn-2-one, and the cyclic products thereby obtained can be transformed into trans-fused bicyclic compounds with high levels of substitution and functionality. Three new C-C or C-N bonds, two new rings, two to four new stereocenters, and one or two new quaternary centers are created in this novel double annulation of two acyclic, readily available starting materials. Examples of the synthesis of trans-decalins, trans- hydrindanes, and trans-perhydroindoles are presented. Methods for converting the nitro groups in the double Michael and double annulation products into other groups are also described.

Original languageEnglish
Pages (from-to)7173-7177
Number of pages5
JournalJournal of Organic Chemistry
Issue number19
StatePublished - Sep 17 1999

ASJC Scopus subject areas

  • Organic Chemistry


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