Asperlicin Explained

Asperlicin is a mycotoxin, derived from the fungus Aspergillus alliaceus. It acts as a selective antagonist for the cholecystokinin receptor CCK_A,^{[1] [2] [3]} and has been used as a lead compound for the development of a number of novel CCK_A antagonists with potential clinical applications.^{[4] [5] [6] [7]} He et al. 1998 present a synthesis from aryl iodide and vinyl iodide.^[8]

References

1. Chang RS, Lotti VJ, Monaghan RL, Birnbaum J, Stapley EO, Goetz MA, Albers-Schönberg G, Patchett AA, Liesch JM, Hensens OD, et al. A potent nonpeptide cholecystokinin antagonist selective for peripheral tissues isolated from Aspergillus alliaceus. Science. 1985 Oct 11;230(4722):177-9.
2. Goetz MA, Lopez M, Monaghan RL, Chang RS, Lotti VJ, Chen TB. Asperlicin, a novel non-peptidal cholecystokinin antagonist from Aspergillus alliaceus. Fermentation, isolation and biological properties. Journal of Antibiotics (Tokyo). 1985 Dec;38(12):1633-7.
3. Liesch JM, Hensens OD, Springer JP, Chang RS, Lotti VJ. Asperlicin, a novel non-peptidal cholecystokinin antagonist from Aspergillus alliaceus. Structure elucidation. Journal of Antibiotics (Tokyo). 1985 Dec;38(12):1638-41.
4. Bock MG, DiPardo RM, Rittle KE, Evans BE, Freidinger RM, Veber DF, Chang RS, Chen TB, Keegan ME, Lotti VJ. Cholecystokinin antagonists. Synthesis of asperlicin analogues with improved potency and water solubility. Journal of Medicinal Chemistry. 1986 Oct;29(10):1941-5.
5. Evans BE, Rittle KE, Bock MG, DiPardo RM, Freidinger RM, Whitter WL, Gould NP, Lundell GF, Homnick CF, Veber DF, et al. Design of nonpeptidal ligands for a peptide receptor: cholecystokinin antagonists. Journal of Medicinal Chemistry. 1987 Jul;30(7):1229-39.
6. Van der Bent A, Ter Laak AM, IJzerman AP, Soudijn W. Molecular modelling of asperlicin derived cholecystokinin A receptor antagonists. European Journal of Pharmacology. 1992 Aug 3;226(4):327-34.
7. Lattmann E, Billington DC, Poyner DR, Howitt SB, Offel M. Synthesis and evaluation of asperlicin analogues as non-peptidal cholecystokinin-antagonists. Drug Design and Discovery. 2001;17(3):219-30.
8. Nakamura . Itaru . Yamamoto . Yoshinori . Transition-Metal-Catalyzed Reactions in Heterocyclic Synthesis . . American Chemical Society (ACS) . 104 . 5 . 2004-02-21 . 0009-2665 . 10.1021/cr020095i . 2127–2198. 15137788 .