The structure and synthesis of rishitinol, a new sesquiterpene alcohol from diseased potato tubers

✍ Scribed by N. Katsui; Akira Matsunaga; K. Imaizumi; T. Masamune; K. Tomiyama

• Publisher: Elsevier Science
• Year: 1971
• Tongue: French
• Weight: 211 KB
• Volume: 12
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)96365-8

✦ Synopsis

In a continuing study on rishitin (2), we have isolated a new sesquiterpene alcohol in 0.0001 $ from tuber tissues of white potatoes (Solanum tuberloeum and 2. demiseum) infected by an incompatible race of phytonhthora infestans. We describe herewith the structure of the alcohol, designated as rishitinol, as well as the total synthesis of its racemic form. Rishitinol (I) Rishitinol (I), m.p. 127-12q", Riahitin (a)D +47O (CHC13), was analyzed for C15H2202 (R+ 234) (3) and resisted acetylation (Ac20-Py, room temp., 2 days) and oxidation with HI04 (room temp., 1 day). The VV, IR and NklR spectral data indicated that I contained the following structural units: tetra-substituted benzene (probably 1,4-dimethyl-2,3-dimethylene aub6tituted benzene (4)) (Xf:F