Singlet oxygen in synthesis. Formation of d,l- and meso-isochrysohermidin from a 3,3′-bipyrrole precursor

✍ Scribed by Harry H. Wasserman; Vincent M. Rotello; Roger Frechette; Robert W. DeSimone; Ji Uk Yoo; Carmen M. Baldino

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 651 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(97)90387-2

✦ Synopsis

A synthesis of the d,l and meso forms of isochrysohem-ridin 3 is outlined which employs the singlet oxygen oxidation of pyrroles as the key step.

The bipyrrole precursor 8 was synthesized from a 3-hydroxy monopyrrole which, in turn, was prepared by addition of methylamine to a vinyl vicinal tricarbonyl.