Synthesis and absolute stereochemistry assignment of enantiopure dihydrofuro-and dihydropyrano-quinoline alkaloids

…, JG Carroll, D Mackerracher, JF Malone

文献索引：Boyd, Derek R.; Sharma, Narain D.; Barr, Stephen A.; Carroll, Jonathan G.; Mackerracher, Donald; Malone, John F. Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 20 p. 3397 - 3405

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被引用次数: 53

摘要

The chiral quinoline alkaloids platydesmine 3, platydesmine methosalt 4 and edulinine 9, have been synthesised in enantiopure form via asymmetric dihydroxylation of the achiral alkaloid atanine 1. Chromatographic separation of MTPA diastereoisomers 20 formed from racemic bromohydrin derivatives of atanine 1 was a key step in the synthesis of geibalansine 7, edulinine 9, ribalinine 10, Ψ-ribalinine 11 and araliopsine 12 as single ...