title: Total synthesis and biosynthesis of the paraherquamides: an intriguing story of the biological Diels-Alder construction.
abstract: The syntheses and biosyntheses of the paraherquamide and brevianamide families of prenylated indole-derived alkaloids are reviewed. It has been proposed that the unique bicyclo[2.2.2]diazaoctan ring system that is common to this family of natural products, arises by a biological intramolecular Diels-Alder cycloaddition reaction. Both synthetic approaches and total syntheses of several members of this family of natural products are reviewed. The biosynthesis of these alkaloids has also constituted an active area of research and the current state of knowledge on the biosynthesis of these natural products are reviewed.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, 80523, USA. rmw@chem.colostate.edu
authors.forename: Robert Michael
authors.initials: RM
authors.lastname: Williams
mesh_terms: D000470:Alkaloids / Q000096:biosynthesis / Q000138:chemical synthesis* / Q000737:chemistry; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D010879:Piperazines; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000470:Alkaloids; D001643:Bridged Bicyclo Compounds; D007211:Indoles; D007212:Indolizines; D010879:Piperazines; D013141:Spiro Compounds; C109708:aspergillimide; C463619:austamide; C084043:VM 55599; C103037:marcfortine A; C063985:paraherquamide