A revised structure of pederin

✍ Scribed by Takeshi Matsumoto; Mitsutoshi Yanagiya; Sawae Maeno; Seiichi Yasuda

• Book ID: 104215319
• Publisher: Elsevier Science
• Year: 1968
• Tongue: French
• Weight: 210 KB
• Volume: 9
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)75458-x

✦ Synopsis

A struotural formula 1 has been assigned to the insect poison pederin, C25H4509N, by Cardsni et al.2) However, spectroscopic evidence indicates that it should be represented rather by a revised structure 8. 1 OR at C-3 instead of C-4. 2 revised structure; OH at C-4. * Pa&s due mainly to the A part (near T 6.15) are further split to form a multiplet. 6300 No.60 Since the moiety must have a skeleton with only eleven carbon atoms, it should contain 12 rather than 2 and the quarternary carbon atom in ll, l2, 16 and g should be identical. The partial formula is thus extended to 18. Further, since in the mass spectrum of pederin, ?CH3 -CH2-CH-CH2-OCH7 22 22 the dominant peaks at m/e 439 (M-2xMeOH), 394 (M-2xMeOH-CH20CH3) and 336 (M-2xMeOH-2) in the high mass region point to the presence of Ip and Rl has been shown to be methyl, 2) the structure 2 is concluded as the most possible expression for pederin. 3) Acknowledgement: The authors express their sincere thanks to Dr. Junji Kawashima for collection of a large amount of Paederus fuscipes Curt, to Drs. Toru Hino (Research Institute for Radiation Medicine) and Kenkichi Nuke&a (Toyo Rayon Co.) for measurement of 100 MHz n m r spectra and to Mr. Isao Sato (Hitachi Co.) for measurement of mass spectra.