Sulphur Analogues of Deoxyvasicinone

Abstract

Abstract The synthesis of the 2‐thioanalogue of deoxyvasicinone ( 1 ) 5 and some higher analogues 6 and 7 are described. Oxidation of these heterocycles with 3‐chloroperoxybenzoic acid gave the sulphoxides 12 , 13 and 14 which underwent facile Pummerer rearrangement to yield, after deacetylation, the alkanols 18 , 19 and 20 . Under more vigorous oxidising conditions 5 and 6 were oxidatively ring opened to yield the sulphonic acids 21 and 22 whereas 7 gave the sulphone 23 .