Total synthesis of (-)-Ampullicin and (+)-lsoampullicin two growth regulators from Ampulliferina sp. no. 27

Article abstract of DOI:10.1016/0040-4039(95)01625-R

The growth regulators (-)-Ampullicin (1) and (+)-isoampullicin (2) have been synthesized utilizing carbaldehyde (25) as the chiral source and N-tertbutoxycarbonyl-3-methyl-2-(trimethylsiloxy)pyrrole (33) as the five-carbon homologative reagent. The synthesis of (1) and (2) is discussed in the context of retrosynthetic analysis. Carbaldehyde (25), has been prepared from both enantiomers of carvone, either (7) or (9), by application of a 15-step sequence with 4.7% and 5.4% overall yields respectively.