Synthesis of Sabina δ-Lactones and Sabina δ-Lactams from (+)-Sabinene
AUSTRALIAN JOURNAL OF CHEMISTRY（2013）
摘要
Two sabina -lactones (3 and 4) were obtained in a two-step synthesis from (+)-sabinene (1). The oxidation of (+)-sabinene (1) with potassium permanganate and sodium periodate to (-)-sabina ketone (2) was the first step. In the second step, the ketone obtained was subjected to chemical and microbial Baeyer-Villiger oxidation. Chemical Baeyer-Villiger oxidation of this ketone afforded two -lactones 3 and 4 whereas microbial Baeyer-Villiger oxidation afforded only abnormal' -lactone 4. (-)-Sabina ketone was also the starting material for the synthesis of new -lactams (7 and 8). They were obtained by Beckmann rearrangement of sabina ketone oximes 5a and 5b. An attempt to separate (-)-sabina ketone oximes 5a and 5b is also presented.
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关键词
combinatorial chemistry,self assembly,nanotechnology,spectroscopy,pharmaceutical chemistry,quantum chemistry,peptide,density functional theory,kinetics,reaction mechanisms,ab initio calculations,amino acids,proteins,biological chemistry,combinatorial,physical chemistry,biocatalysis,computational chemistry,mass spectrometry,interfaces,ionic liquids,organic chemistry,crystal structures,surface chemistry,enzymes,analytical chemistry,supramolecular chemistry,educational,inorganic chemistry,crystallography,electrochemistry,polymer chemistry,green chemistry,photochemistry,biosensors,macromolecules,structure,sensors,catalysis,colloids,medicinal chemistry
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