Biomimetic syntheses of polyketide aromatics from reaction of an orsellinate anion with pyrones and a pyrylium salt

Abstract

Orsellinate anion (12) shows highly regioselective attack on pyrones (13), (22), and (30), and the products were simply converted into derivatives of the polyketides: toralactone (19), 6-hydroxyrnusizin (26), and eleutherinol (32); although reaction of the anion (12) with the pyrylium salt (33) is less selective, the major product (34) can give derivatives of either alternariol (36) or rubrofusarin (37) in regiospecific biomimetic reactions.