Synthesis of natural products containing spiroketals via intramolecular hydrogen abstraction.
Although known for over a quarter of a century, the oxidative radical cyclisation route to spiroketals has found limited use in natural product synthesis in comparison to classical approaches. Its successful application in this field of research forms the subject of this perspective.
Sperry
Jonathan
J
Department of Chemistry, University of Auckland, 23 Symonds Street, Auckland. New Zealand.
Liu
Yen-Cheng William
YC
Brimble
Margaret A
MA
D000871:Anthelmintics / Q000138:chemical synthesis / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry; D001572:Benzofurans / Q000138:chemical synthesis / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis / Q000737:chemistry; D002922:Ciguatoxins / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D004987:Ethers / Q000138:chemical synthesis / Q000737:chemistry; D004988:Ethers, Cyclic / Q000138:chemical synthesis / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry*; D007559:Ivermectin / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D008387:Marine Toxins; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis / Q000737:chemistry; D010084:Oxidation-Reduction; D010619:Phenazines / Q000138:chemical synthesis / Q000737:chemistry; D010749:Phosphoprotein Phosphatases / Q000138:chemical synthesis / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D000095662:Polyether Polyketides
D000871:Anthelmintics; D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D001572:Benzofurans; D001688:Biological Products; D001952:Bridged-Ring Compounds; D002922:Ciguatoxins; D004987:Ethers; D004988:Ethers, Cyclic; D005663:Furans; D006859:Hydrogen; D007559:Ivermectin; D008387:Marine Toxins; D010080:Oxazoles; D010619:Phenazines; D010749:Phosphoprotein Phosphatases; D011714:Pyrans; D013141:Spiro Compounds; C526075:5-hydroxy-7-methoxy-3-(5-(2-methyl-1,6-dioxaspiro(4,5)dec-7-yl)pentyl)-2-benzofuran-1(3H)-one; C425408:CP44,161; C456580:bistramide C; C520774:spiroketal; C467770:spirolide B; C467769:spirolide D; C010327:salinomycin; D000095662:Polyether Polyketides; C019264:avermectin; C059041:calyculin A; C013612:narasin