Heteroaromatics: The Zhu Synthesis of Anibamine B
Chemexpress Kegong Ji of the Northwest Agricultural & Forestry University used a Cu catalyst to cyclize the alkyne 1 to the furan 2 (Org. 8-Hydroxyoctanoic acid In stock Chem. Front. 2023,…
Alkaloid Synthesis: Tabertinggine (She), Kopisinine (Ruijter), Sieboldine A (Yao), Rhazinicine (Miranda), Brevianamide A (Gagosz), Daphlongamine E (Xu)
Tabertinggine (4) was isolated from the Mayasian shrub Tabernaemontana corymbosa, the dwarf pinwheel. Xuegong She of Lanzhou University assembled the key tetracyclic intermediate 3 by the BINOL-derived phosphoric acid mediated…
C-O Ring Construction: Spiroapplanatumine O (Jahn), Alcyonolide (Hosokawa), Wentilactone A (Xu/Yu), Aquilanol A (Stathakis), Thallusin (Arndt), Neobraclactone C (Cheng/Liu)
Spiroapplanatumine O (3) was isolated from Ganoderma applantum, a wood-decaying fungus that is widely used in traditional medicinal chemistry. Ullrich Jahn of the Institute of Organic Chemistry and Biochemistry of…
C-O Ring Construction: Ophiofuranone A (Schobert), Galanthamine (Brown),
Spirooliganone A (Morita), Microansamycin H (Sittihan), Gymnothelignan N (Lee), 3(11)-Epoxyhypoestenone (Wang/Chen) Ophiofuranone A (3) was isolated from the endolichenic fungus Ophiospaerella korrae. Rainer Schobert of the University Bayreuth prepared the…
Metal-mediated C-C Ring Construction: The Sarpong Synthesis of 15-Hydroxypatchoulol
John P. Price of 3-Chloro-1H-pyrazole Wolfe of the University of Michigan constructed the cyclobutene 3 by coupling the enol triflate 1 with diethyl malonate 2 (Org. Lett. 2022, 24, 8208.…
Oxidation: The Vanderwal Synthesis of 7,20-Diisocyanoadociane
Masato Matsugi of Meijo University prepared the carbamoyl azide 2 by reaction of the hydroxamic acid 1 with diphenyl phosphorazidate (Tetrahedron Lett. PMID:32261617 2022, 95, 153727. DOI: 10.1016/j.tetlet.2022.153727). Yan Zhao…
C-N Ring Construction: The Hayashi Synthesis of Quinine
Benjamin Darses of the Université Grenoble-Alpes and Marie Sircoglou and Philippe Dauban of the Université Paris-Saclay effected the enantioselective aziridination of the terminal alkene 1 with 2, leading to 3…
Benzene Derivatives: The Dudley Synthesis of Coprinol
Hongjian Lu of Nanjing University used an Ir catalyst to mediate the regioselective ortho amination of the benzamide 1, leading to the protected anthranilamide 2 (J. Org. 574007-66-2 structure Chem.…
Enantioselective Synthesis of Alcohols and Amines: The Huang/Chen Synthesis of
α-Tocopherol Pinhong Chen and Guosheng Liu of the Shanghai Institute of Organic Chemistry developed a protocol for the enantioselective conversion of a terminal alkene 1 to the secondary benzoate 2…
Stereoselective Construction of Carbocyclic Rings
Carbocyclic rings, unlike saturated heterocyclic rings, are not susceptible to the hepatic activation that is the basis of much drug toxicity. To pave the way for pharmaceutical discovery based on…