Literature DB >> 18600283

Stereochemistry and rearrangement reactions of hydroxylignanolactones.

Barbara Raffaelli1, Monika Pohjoispää, Tapio Hase, Christine J Cardin, Yu Gan, Kristiina Wähälä.   

Abstract

Various conflicting data on the rearrangement and absolute stereochemistry of hydroxylignano-9,7'-lactones are resolved using 18O labeled compounds, also confirmed by an X-ray analysis of a pure lignano-9,7'-lactone enantiomer, obtained for the first time. Under NaH/DMF rearrangement conditions a silyl protected hydroxylignano-9,9'-lactone underwent an unexpected silyl migration.

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Year:  2008        PMID: 18600283     DOI: 10.1039/b801593g

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  1 in total

1.  Model Studies To Access the [6,7,5,5]-Core of Ineleganolide Using Tandem Translactonization-Cope or Cyclopropanation-Cope Rearrangements as Key Steps.

Authors:  Jennifer L Roizen; Amanda C Jones; Russell C Smith; Scott C Virgil; Brian M Stoltz
Journal:  J Org Chem       Date:  2017-11-21       Impact factor: 4.354

  1 in total

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