An Ireland−Claisen Approach to Lignans: Synthesis of the Putative Structure of 5-epi-Eupomatilone-6
- 18 May 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (12) , 4185-4191
- https://doi.org/10.1021/jo049817r
Abstract
A novel Ireland−Claisen approach to the putative structure of eupomatilone-6 is described. The rearrangement established the C3 and C4 stereocenters and concomitantly generated a vinyl epoxide. The C5 oxygen was installed by cyclization of the pentenoic acid carboxyl group onto the vinyl epoxide in an SN2‘ fashion to afford the C5-epi stereochemistry. The natural C5 stereochemistry was accessed via a substrate directed dihydroxylation.Keywords
This publication has 5 references indexed in Scilit:
- Synthesis of the Putative Structure of Eupomatilone-6Organic Letters, 2004
- Synthetic approaches to the Manumycin A, B and C antibiotics: The first total synthesis of (+)-Manumycin ATetrahedron, 1999
- Antimitotic natural products and their interactions with tubulinMedicinal Research Reviews, 1996
- Photoinduced Molecular Transformations. 157. A New Stereo- and Regioselective Synthesis of 2,6-Diaryl-3,7-dioxabicyclo[3.3.0]octane Lignans Involving a .beta.-Scission of Alkoxyl Radicals as the Key Step. New Total Syntheses of (.+-.)-Sesamin, (.+-.)-Eudesmin, and (.+-.)-YangambinThe Journal of Organic Chemistry, 1995
- Highly stereoselective synthesis of (2E,4E)-dienamides and (2E,4E)-dienoates via a double elimination reactionTetrahedron Letters, 1986