Studies Towards the Synthesis of Salvinorin A
AUSTRALIAN JOURNAL OF CHEMISTRY（2006）
摘要
Salvinorin A 1, a psychoactive neoclerodane diterpenoid from the Mexican sage S. divinorum, has gained interest as a selective kappa-opioid receptor agonist. Non-racemic 3-furylamines 9a and 9b have been prepared from (+)-pseudoephedrine and (-)-ephedrine for application in the stereoselective synthesis of the ketone ring of 1. Diels-Alder reaction of 9b with methyl acrylate in aqueous media, followed by selective ether bridge cleavage, has allowed access to the cyclohexenone 17 with preservation of stereochemistry at C2. A model route to the lactone ring has also been achieved through a one-pot deconjugation/esterification procedure of 2-bromocrotonyl chloride 20 to the furyl alcohol 19 followed by Reformatski-mediated ring closure.
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关键词
nanotechnology,biocatalysis,combinatorial chemistry,organic chemistry,reagents,interfaces,pharmaceutical chemistry,proteins,combinatorial,electrochemistry,surface chemistry,computational chemistry,catalysis,analogs,sensors,polymer chemistry,kinetics,reaction mechanisms,crystallography,medicinal chemistry,analytical chemistry,green chemistry,educational,structure,crystal structures,ab initio calculations,photochemistry,quantum chemistry,mass spectrometry,amino acids,self assembly,density functional theory,hallucinogens,spectroscopy,inorganic chemistry,supramolecular chemistry,biosensors,ionic liquids,enzymes,macromolecules,biological chemistry,colloids,peptide,physical chemistry
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