Total Synthesis of Eupomatilones 4 and 6: Structurally Rearranged and Atropisomerically Fluxional Lignan Natural Products
- 1 October 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 6 (22) , 4025-4028
- https://doi.org/10.1021/ol048333e
Abstract
A convergent and diastereocontrolled total synthesis of eupomatilones 4 and 6 is reported and was based on a diastereoselective hydroboration/oxidation sequence and a convergent Lipshutz biarylcuprate cross-coupling reaction. The structure of eupomatilone 6 is revised.Keywords
This publication has 27 references indexed in Scilit:
- An Ireland−Claisen Approach to Lignans: Synthesis of the Putative Structure of 5-epi-Eupomatilone-6The Journal of Organic Chemistry, 2004
- Synthesis of the Putative Structure of Eupomatilone-6Organic Letters, 2004
- An Approach to the Synthesis of the EupomatilonesOrganic Letters, 2001
- Effect of the acidic component on the Mitsunobu inversion of a sterically hindered alcoholThe Journal of Organic Chemistry, 1994
- Halogenation Using N-Halogenocompounds. I. Effect of Amines on ortho-Bromination of Phenols with NBSBulletin of the Chemical Society of Japan, 1993
- Efficacious modification of the mitsunobu reaction for inversions of sterically hindered secondary alcoholsTetrahedron Letters, 1991
- Constituents of Eupomatia Species. xiv. The Structures of Eupomatilone-1, -2, -3, -4, -5, -6 and -7 Isolated From Eupomatia BennettiiAustralian Journal of Chemistry, 1991
- Constituents of Eupomatia Species. XII. Isolation of Constituents of the Tubers and Aerial Parts of Eupomatia bennettii and Determination of the Structures of New Alkaloids From the Aerial Parts of E. bennettii and Minor Alkaloids of E. laurinaAustralian Journal of Chemistry, 1991
- The Synthesis of Hydroxybenzaldehydes from Bromobenzaldehydes via Lithiated Schiff's Bases. Preparation of 5-Hydroxypiperonal and Related CompoundsSynthetic Communications, 1981
- Ortho bromination of phenolsThe Journal of Organic Chemistry, 1967