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Marisa Mena 《Tetrahedron》2006,62(39):9166-9173
Birch reduction of homotyramines with a syn-β-amino alcohol unit followed by acid treatment of formed dihydroanisole derivatives gives polysubstituted enantiopure cis-decahydroquinolines. The stereoselectivity of the process differs if the hydroxyl group is free or protected. The procedure allows the synthesis of 7-oxodecahydroquinolines embodying four stereogenic centres with the same relative configuration as that of lepadins F and G. 相似文献
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Edith J. Banner 《Tetrahedron letters》2004,45(22):4411-4414
The Diels-Alder precursor was constructed from readily available d-glutamic acid utilizing a series of functional group transformations. The stereocenter of the amino acid provided the desired stereochemistry at C2 and diastereoselectively directed the intramolecular Diels-Alder cyclization. This simultaneously generated the three remaining stereocenters and yielded a bicyclic intermediate with all four stereocenters of the target decahydroquinoline 275B. 相似文献
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Marisa Mena 《Tetrahedron》2005,61(34):8264-8270
Syntheses of enantiopure 3-acetoxy-2-methyldecahydroquinolines are accomplished by coupling cyclohexenyllithium 3 with α-amino epoxides and an aminocyclization of 2-(3-aminoalkyl)cyclohexenones (i.e., 5 and 9) as the key steps. The procedure allows the incorporation of alkyl substituents at C(5) to give enantiopure 2,3,5-trisubstitued decahydroquinolines. 相似文献
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