Synthesis of longithorone B, a sixteen-membered farnesylated p-benzoquinone

✍ Scribed by Tadahiro Kato; Kentaro Nagae; Masahiro Hoshikawa

• Book ID: 104260847
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 230 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(99)00049-0

✦ Synopsis

The intramolecular coupling reactions at the C-1 position of the 10Z-farnesyl moiety appended at the 2'-position of 4'-methoxy phenol derivatives were examined with the aid of Hf(OTf)4 and LiC104. When the phenol was protected with a TBDMS group, meta coupling predominated while para coupling occurred efficiently when protected with a pivaloyl group. The para-coupled product was transformed to longithorone B, recently isolated from a tunicate.