Enantioselective synthesis of fusarentin methyl ethers: Insecticidal metabolites of Fusarium larvarum

Article abstract of DOI:10.1016/0040-4039(96)01823-0

Fusarentin 4,5-dimethyl ether (1) and its 4-desmethoxy analogue are synthesised via acylation of the benzylic anion of N,N-dimethyl-2,3,4-trimethoxy-6-methylbenzamide (9) and N,N-dimethyl-2,4-dimethoxy-6-methylbenzamide (8) with N-methoxy-N-methyl-(S)-3-tert-butyldimethylsilyloxyhexanamide (13): Subsequent reduction of ketone (15) to the anti-1,3-diol (16) and acid catalysed cyclisation gives (1).