23680-40-2Relevant articles and documents
Synthesis of Epibatidine Analogues by Pyrrole Diels–Alder Reactions: Rapid Access to Azabicyclo[2.2.1]heptane and 3,8-Diazabicyclo[3.2.1]octane Scaffolds for Library Synthesis
Murray, Alexander T.,Packard, Emma,Nortcliffe, Andrew,Lewis, William,Hamza, Daniel,Jones, Geraint,Moody, Christopher J.
, p. 138 - 148 (2017)
Analogues of the nicotinic acetylcholine antagonist epibatidine, suitable for diversification, were synthesized by application of a pyrrole Diels–Alder strategy, allowing rapid generation of azabicyclo[2.2.1]heptane bicyclic cores. Further molecular complexity could be accessed by using intramolecular Diels–Alder reactions, or ring expansion by ozonolysis–reductive amination chemistry. Scaffolds were designed such that they could be orthogonally deprotected, yielding three points of diversity for library synthesis, exemplified by 24 compounds synthesized from four cores.
Development of an enolate alkynylation approach towards the synthesis of the taiwanschirin natural products
Christensen, Kirsten E.,Donohoe, Timothy J.,Haughey, Maxwell B.,Poole, Darren L.
, p. 13392 - 13397 (2021/11/01)
Through the use of model studies, an approach was conceived towards the synthesis of the taiwanschirin family of natural products. These are structurally complex compounds which represent highly challenging and biologically active targets for total synthesis. This work describes a successful synthesis of the complex taiwanschirin fused [8,6,5] core through a novel alkynylation reaction coupled with an intramolecular Heck reaction used to construct the 8-membered ring.
Intermolecular cyclotrimerization of haloketoalkynes and internal alkynes: Facile access to arenes and phthalides
Silvestri,Oakdale
supporting information, p. 13417 - 13420 (2020/11/10)
A highly chemo-and regioselective cyclo(co)trimerization between 3-halopropiolamides and symmetrical internal alkynes is reported. The reaction is catalyzed by CpRuCl(COD) and proceeds under air at ambient temperature in ethanol with no additional precautions. Iodo-, bromo-, and chloropropiolamides, esters, and ketones are viable coupling partners and, in a 2?:?1 stoichiometry relative to internal alkyne, yield fully-substituted arenes in a single step. The highest regioselectivities (96% single isomer) were observed when employing 2° and 3°-halopropiolamides. A mechanistic hypothesis accounting for this selectivity is proposed. Notably, by using 1,4-butynediol as the internal alkyne, in situ lactonization following [2+2+2]-cycloaddition generates therapeutically-relevant phthalide pharmacophores directly. This journal is
6-HYDROXY-8-OXATRICYCLO[3.2.1.02,4]OCTANE-2-CARBOXAMIDE DERIVATIVES FOR INDUCING CHONDROGENESIS FOR TREATING JOINT DAMAGE
-
Page/Page column 13; 24, (2020/07/06)
The present invention provides 6-hydroxy-8- oxatricyclo[3.2.1.02,4]octane-2-carboxamide derivatives of Formula (1) wherein the variables are as defined herein. The present invention further provides pharmaceutical compositions comprising such compounds. The compounds are used for inducing chondrogenesis, in methods of treating or preventing joint damage, resulting from joint injury or arthritis, and for inducing hyaline cartilage production. The present description discloses the preparation of exemplary compounds as well as pharmacological data thereof (examples 1 to 82; tables 1 and 2). An exemplary compound is e.g. rac-(1R,2R,4S,5R,6S)-4-(2- fluoropyridin-4-yl)-6-hydroxy-N-(4-(trifluoromethyl)pyridin-2-yl)-8- oxatricyclo[3.2.1.02,4]octane-2-carboxamide (example 1).
