2017
DOI: 10.1016/j.tetasy.2017.10.023
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A convergent approach towards the synthesis of the 2-alkyl-substituted tetrahydroquinoline alkaloid (−)-cuspareine

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Cited by 2 publications
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“…Basaveswara Rao, Akula, et al also demonstrated an intramolecular variant of this approach. In their synthesis, the precursor alcohol 172 was assembled from O ‐isopropylidene glyceraldehyde 170 and in the key step, exposure of 172 to DIAD and PPh 3 resulted in intramolecular Mitsunobu reaction to give 2‐substituted 1,2,3,4‐tetrahedroquinoline derivative 173 in 78 % yield.…”
Section: Discussionmentioning
confidence: 99%
“…Basaveswara Rao, Akula, et al also demonstrated an intramolecular variant of this approach. In their synthesis, the precursor alcohol 172 was assembled from O ‐isopropylidene glyceraldehyde 170 and in the key step, exposure of 172 to DIAD and PPh 3 resulted in intramolecular Mitsunobu reaction to give 2‐substituted 1,2,3,4‐tetrahedroquinoline derivative 173 in 78 % yield.…”
Section: Discussionmentioning
confidence: 99%
“…Encouraged by these interesting biological properties, many chemists contributed to the development of asymmetric synthesis of these tetrahydroquinoline motifs. Bearing in mind that the main challenge is the asymmetric generation of the secondary amine, a variety of reactions have been utilized as key steps, with most syntheses relying on asymmetric catalytic hydrogenation of quinolines . Another general approach for the construction of the chiral secondary amine by allylic substitution was developed by Helmchen using an Ir/phosphoramidite-based catalyst system. , …”
mentioning
confidence: 99%