Enantioselective synthesis of heliannuol E; structural consideration of natural molecule

✍ Scribed by Fuminao Doi; Takahisa Ogamino; Takeshi Sugai; Shigeru Nishiyama

• Book ID: 104253789
• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 154 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(03)01094-3

✦ Synopsis

Heliannuol E 1, isolated from Helianthus annuus L. cv. SH-222, was successfully synthesized in both optically active forms, by novel ring-expansion reaction of the corresponding spirodienone derivatives 8 and 17, which were produced from 7 and 16 under anodic oxidation conditions. The absolute structure of the natural product was determined to have R-configuration at the benzylic position.