A stereospecific synthesis of chaloxone

✍ Scribed by Tomas Fex

• Book ID: 104244091
• Publisher: Elsevier Science
• Year: 1981
• Tongue: French
• Weight: 96 KB
• Volume: 22
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)92976-4

✦ Synopsis

one, has been synthesised from benzoquinone via a diepoxide. Chaloxone (l), together with the methyl ester of (+)-3,4_anhydroshikimic acid (z), was isolated from the fungus Chalara microspora (Corda) Hughes. 132 CH30 :x, CO2CH, The synthesis of chaloxone (1) involves the introduction of many different functional groups, with the epoxide trans to the hydroxyl group. A synthetic strategy was chosen, whereby this configuration should be obtained by an epoxide elimination (e.g. A+ 3) in the final stage of the reaction sequence. A synthesis of 5 described in a publication by Altenbach et al3 --.

made it possible to test the idea. Furthermore, the symmetry of 2 is highly favourable for the scheme.