| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5268757 | Tetrahedron Letters | 2012 | 4 Pages |
Abstract
The first total synthesis of hibarimicinone has been achieved. The polyhydroxydecalin moieties (AB and GH rings) have been synthesized from sulfonylenone 4 derived from d-arabinose. The chiral biaryl 20 was coupled with two polyhydroxydecalins 11 by Michael–Dieckmann type condensation to give the eight rings system. Aromatization and oxidation with Ag+ gave quinone 24, and the subsequential transannular etheration gave the hibarimicinone skeleton. Deprotection and tautomerization were performed in one pot to give hibarimicinone (1).
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
