2016
DOI: 10.1021/jacs.6b07846
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Enantioselective Synthesis of (+)-Peganumine A

Abstract: A gram-scale enantioselective total synthesis of (+)-peganumine A was accomplished in 7 steps from commercially available 6-methoxytryptamine. Key steps included (a) a Liebeskind-Srogl cross-coupling; (b) a one-pot construction of the tetracyclic skeleton from an ω-isocyano-γ-oxo-aldehyde via a sequence of an unprecedented C-C bond forming lactamization and a transannular condensation; (c) a one-pot organocatalytic process merging two achiral building blocks into an octacyclic structure via a sequence of enant… Show more

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Cited by 87 publications
(58 citation statements)
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“…Treatment of indole 28 with LiTMP followed by the addition of tributyltin chloride afforded C‐2 stannylated indole 29 . Palladium‐catalyzed Liebeskind–Srogl coupling between 29 and thioester 30 under our recently optimized conditions provided the desired coupling adduct 31 , which underwent β‐elimination during flash column chromatography (eluent containing Et 3 N) to directly furnish the desired diene 32 in 90 % yield on a multigram scale. It is interesting to note that coupling of 29 with S ‐phenyl prop‐2‐enethioate gave 32 in a rather poor and irreproducible yield due to facile polymerization of this conjugated thioester.…”
Section: Resultsmentioning
confidence: 97%
“…Treatment of indole 28 with LiTMP followed by the addition of tributyltin chloride afforded C‐2 stannylated indole 29 . Palladium‐catalyzed Liebeskind–Srogl coupling between 29 and thioester 30 under our recently optimized conditions provided the desired coupling adduct 31 , which underwent β‐elimination during flash column chromatography (eluent containing Et 3 N) to directly furnish the desired diene 32 in 90 % yield on a multigram scale. It is interesting to note that coupling of 29 with S ‐phenyl prop‐2‐enethioate gave 32 in a rather poor and irreproducible yield due to facile polymerization of this conjugated thioester.…”
Section: Resultsmentioning
confidence: 97%
“…The synthesis of natural and synthetic analogues of Kumujian C has been achieved by several research groups and thesec om-poundsh ave been utilized for the synthesis of D-ring-containing b-carboline frameworks through C1-N2a nd C1-N9 cyclization reactions. In addition, the synthetic potentialo ft he formyl group has been explored for the construction of b-carboline- [20] AsianJ.O rg.C hem. 2018, 7,6-36 www.AsianJOC.org 2018 Wiley-VCH Verlag GmbH &Co. KGaA, Weinheim tethered frameworks.…”
Section: Synthesis and Application Of 1-formyl-b-carbolinesmentioning
confidence: 99%
“…1. [9][10][11][12][13][14][15] Recent reports from our group have described highly enantioselective Michael addition chemistry of various substituted TKP systems. [16][17][18] The chiral TKPs are generated in highly diastereo-and enantioselective form, and are amenable to fruitful regioselective manipulation to give attractive natural product like structures.…”
mentioning
confidence: 99%