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

Article abstract of DOI:10.1016/S0040-4039(99)00049-0

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 LiClO₄. 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.