Stereo- and Regioselective Synthesis of Tricyclic Spirolactones by Diastereoisomeric Differentiation of a Collective Key Precursor

Viviana Valerio, Yelena Mostinski, Ramesh Kotikalapudi, Dmitry Tsvelikhovsky

Research output: Contribution to journalArticlepeer-review

Abstract

A general, parallel, and collective synthesis of 5/5/5- and 5/5/6-ring fusion topologies of tricyclic spiranoid lactones through the controlled cyclizations of easily accessible, common key precursors is described. The rapid composition of key cycloalkyl methylene precursors yielded an assembly of bicyclic diastereoisomeric iodolactones, which were individually converted into a wide range of tricyclic, angularly fused spiranoid lactones in a regioselective and stereodirected fashion through the diastereoisomeric differentiation of a collective key precursor. The critical stereochemical assignment of the bicyclic starting materials, as well as the tricyclic targets, was confirmed by X-ray crystal structure determination.

Original languageAmerican English
Pages (from-to)2640-2647
Number of pages8
JournalChemistry - A European Journal
Volume22
Issue number8
DOIs
StatePublished - 18 Feb 2016

Keywords

  • cyclization
  • diastereoselectivity
  • lactones
  • regioselectivity
  • spiro compounds

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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