O-Methylasparvenone, a Nitrogen-free Serotonin Antagonist

Article abstract of DOI:10.1016/S0968-0896(97)00160-0

O-Methylasparvenone (1) and asparvenone (2) were isolated from an Aspergillus parvulus Smith broth in a microbial screening for 5-HT_2C ligands and found to be 5-HT_2C antagonists.They represent the first nitrogen-free serotonin ligands.The absolute configuration of 1 was determined to be S by X-ray analysis of the corresponding Mosher-ester.A short and efficient synthesis of rac-1 was developed.This protocol was applied to the synthesis of derivatives of 1 and a structure-affinity relationship was established.