Synthesis of Pteroenone and Its Stereoisomers, a Defensive Metabolite of the Abducted Antarctic Pteropod Clione antarctica

✍ Scribed by Hiroki Asao; Yoko Nakamura; Yukito Furuya; Shigefumi Kuwahara; Bill J. Baker; Hiromasa Kiyota

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: German
• Weight: 260 KB
• Volume: 93
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.201000258

✦ Synopsis

Four stereoisomers of (þ)-pteroenone, a defensive metabolite of the abducted Antarctic pteropod Clione antarctica, were synthesized by employing anti-/syn-selective aldol reactions as the key step. These compounds displayed no antifeedant activity against a generally benthic Antarctic fish that does not cooccur with this pteropod.

2 ) Deprotection of the EE group of the corresponding compound 14 (pyridinium p-toluenesulfonate (PPTS), MeOH) gave (þ)-1 with 70% de. 3 ) Direct conversion of thio ester 11 to ketone 14 failed under a variety of Fukuyama coupling conditions and organocopper compounds. Table. Alkylation of 12 Entry Conditions Yield [%]