Artifacts and Natural Substances Formed Spontaneously

ortho-Quinone Methide Cyclizations Inspired by the Busseihydroquinone Family of Natural Products

“…A similar all-carbon intramolecular Diels–Alder reaction of a chromene was used in our recent total synthesis of verrubenzospirolactone . We propose that cyclic enol ether 6 could be an undiscovered natural product and that busseihydroquinone E ( 3 ) and parvinaphthol C ( 4 ) could be artifacts of the isolation process formed by the addition of either EtOH or MeOH, respectively, to 6 . Both the Pentas bussei and Pentas parvifola plant materials were exposed to MeOH, EtOAc, and oxalic-acid-impregnated silica gel in the isolation procedures.…”

Total synthesis of incargranine A

“…This would not necessarily mean that incargranine A (1) is an unimportant artifact of human intervention. 17 It is known, for example, that plants can use glycosidic-metabolites as chemical defense systems, wherein damage to the plant brings gycosidase enzymes into contact with the glycosides to release the active aglycones. 18…”