Stereocontrolled synthesis of highly functionalized cyclohexenes. A short synthesis of a chorismic acid precursor

✍ Scribed by Gary H. Posner; Todd D. Nelson

• Publisher: Elsevier Science
• Year: 1990
• Tongue: French
• Weight: 861 KB
• Volume: 46
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)85582-4

✦ Synopsis

A convenient and mild thermal procedure has been developed for stereoselective 2+4-cycloadditions of electron-rich 1,2-dioxygenated olefins 7 to electron-deficient 3-sulfonyl-2-pyrone 6 allowing isolation of the structurally and stereochemically rich initial bicyclic adducts 8. These bicyclic adducts are shown to be useful building units as exemplified by a very short and high-yield preparation of a chorismic acid precursor.