Progress Toward the Total Synthesis of the Epoxyquinoid Family of Natural Products
Author | : |
Publisher | : |
Total Pages | : 228 |
Release | : 2007 |
ISBN-10 | : OCLC:154309229 |
ISBN-13 | : |
Rating | : 4/5 ( Downloads) |
Download or read book Progress Toward the Total Synthesis of the Epoxyquinoid Family of Natural Products written by and published by . This book was released on 2007 with total page 228 pages. Available in PDF, EPUB and Kindle. Book excerpt: Enyne metathesis is a powerful C-C bond forming reaction that combines an alkene and an alkyne and forms a conjugated 1,3-diene. The scope of enyne metathesis was expanded by combining various alkynes with vinyl ethers. Typically vinyl ethers are poor metathesis substrates, but a method was developed for the synthesis of dienol ethers utilizing ruthenium carbenes. The products of these reactions were subjected to [4+2] cycloaddition conditions to give substituted cyclohexene rings. The epoxyquinoid family is a highly targeted series of natural products. A general method for the synthesis of the core structure of these natural products has been explored. An enyne cross metathesis/ring closing metathesis step was designed as the key reaction to this synthesis. A Darzen's condensation between a chiral [alpha]-alkoxy aldehyde and a chloroacyl oxazolidinone was successfully employed to join two fragments of the molecule as well as to install an epoxide. A highly diastereoselective cuprate addition set the stereochemistry of the first stereogenic center. The early intermediates were prepared via easily scalable organic syntheses procedures including utilizing a carbohydrate as the source of chirality. Ring closing enyne metathesis to form the epoxyquinoid core was evaluated in two epimeric series.