Ylidenebutenolide mycotoxins. Concise syntheses of patulin and neopatulin from carbohydrate precursors

Abstract

Conversion of arabinose 10 to the protected ketone 13 followed by Wittig condensation to 14, acidcatalysed cyclisation (to lactone 16), dehydration and deprotection provides a brief synthesis of the mycotoxic substance patulin 1, which is produced by Penicillium and Aspergillus spp. In a similar manner, the biogenetic precursor to patulin, neopatulin 8, is synthesized from lyxose 25via the key intermediates 24, 28 and 30.