Total synthesis and biosynthesis of the paraherquamides: an intriguing story of the biological Diels-Alder construction.
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.
Williams
Robert Michael
RM
Department of Chemistry, Colorado State University, Fort Collins, 80523, USA. rmw@chem.colostate.edu
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
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