Compound W was isolated from a marine annelid commonly used in Japan as a fish bait, and it was shown to be the substance that gives this organism its observed toxicity to some insects that contact it.
MS (m/z): 151 (relative abundance 0.09), 149 (M+., rel. abund. 1.00), 148
IR (cm-1): 2960, 2850, 2775
1H NMR (δ): 2.3 (s, 6H), 2.6 (d, 4H), and 3.2 (pentet, 1H)
13C NMR (δ): 38 (CH3), 43 (CH2), and 75 (CH)
These reactions were used to obtain further information about the structure of W:
These reactions were used to obtain further information about the structure of W:

NaBHa CEHsCOC Raney Ni