Stereochemistry and rearrangement reactions of hydroxylignanolactones

Raffaelli, B., Pohjoispaa, M., Hase, T., Cardin, C.J. ORCID: https://orcid.org/0000-0002-2556-9995, Gan, Y. and Wahala, K. (2008) Stereochemistry and rearrangement reactions of hydroxylignanolactones. Organic & Biomolecular Chemistry, 6 (14). pp. 2619-2627. ISSN 1477-0520 doi: 10.1039/b801593g

Abstract/Summary

Various conflicting data on the rearrangement and absolute stereochemistry of hydroxylignano-9,7'-lactones are resolved using O-18 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.