Fusicoccin. Part 6. Biosynthesis of fusicoccin from [3-13C]- and (4R)-[4-3H1]-mevalonic acid

Abstract

[3-¹³C]Mevalonic acid lactone has been synthesised from [1-¹³C]acetate and selectively incorporated into positions 3,7,11,15, and 24 of fusicoccin (1a). Four out of a possible five 4-pro-R mevalonoid hydrogen atoms were retained in fusicoccin and fusicoccin J, and three were retained in fusicoccin H. The results are consistent with the cyclisation of a polyprenyl pyrophosphate precursor in a manner different to that previously observed in the biosynthesis of the ophiobolins.