ChemInform Abstract: Sequential Application of Stereoselective syn-Oxidation Methodologies to Natural Product Synthesis: A Potentially Biomimetic Approach to the C12—C21 Bistetrahydrofuran Region of Monensin.
✍ Scribed by F. E. MCDONALD; C. C. SCHULTZ
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 37 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0931-7597
No coin nor oath required. For personal study only.
✦ Synopsis
Sequential Application of Stereoselective syn-Oxidation Methodologies to Natural Product Synthesis: A Potentially Biomimetic Approach to the C 12 -C 21 Bistetrahydrofuran Region of Monensin.
-The bistetrahydrofuran (VII), the C-D ring unit of monensin, is prepared by regio-and enantioselective syn-dihydroxylation of the triene (II), cis-selective syn-oxidative cyclization of the enol (III), and trans-selective syn-oxidative cyclization of the enol (VI). Additionally, it is proposed that the stereochemical pattern of the polyether regions of monensin and lonomycin cannot be correctly produced via VO(acac) 2 -mediated oxidations. -(MCDONALD, F.