Original Articles: 2014 Vol: 6 Issue: 11
Total synthesis of Hirsutellide A
Abstract
The total synthesis of Hirsutellide A was described. Macro cyclisation was successfully performed on the fully deprotected amino acid by Yamaguchi esterification protocol was carried out for the intramolecular cyclisation of the linear hexadepsipeptide to give the coupling product (Hirsutellide A) with the reagents TCBC, Et3N and DMAP in 22% yield. The linear hexapeptide precursor was synthesized in 25% from TBS-phe-ile-N-Me-gly-Cbz by undergoing three reactions with LiOH, CSA, DCC-DMAP respectively. Tripeptide and Dipeptide are synthesized by common coupling reactions, the coupling reagents used are HOBT, EDCI, HOAt, HATU and DIPEA. In addition to two standard amino acids, N-methylated glycine and L-isoleucine, I used an unusual hydroxyl D-phenylalanine amino acid.