Total Syntheses of <i>rac</i>‐ and (+)‐Goniomitine

Park, Eunjoon; Cheon, Cheol Hong

doi:10.1002/adsc.201900801

Cited by 14 publications

(11 citation statements)

References 31 publications

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“…89 An example is the transformation of imine 84 to vinylindole 85, a precursor for the synthesis of (+)-goniomitine (86) (55% over three steps from compound 85, Scheme 22). 90 Other examples of heterocyclic frameworks accessible by the imino-Stetter reaction are benzocarbazoles 91 and indoloquinolizines, which are also a structural motif of several natural products. The latter result from the conversion of amino-cinnamates with pyridinecarbaldehydes via imines 87 (Scheme 23).…”

Section: Imino-stetter Reactionmentioning

confidence: 99%

Cyanide Anions as Nucleophilic Catalysts in Organic Synthesis

Kieslich¹,

Christoffers²

2021

Synthesis

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The nucleophilic addition of a cyanide anion to a carbonyl group is the basis for several cyanide-catalyzed organic reactions, which are summarized in this review. Since cyanide is also a good leaving group, it is an excellent catalyst for transacylation reactions. As an electron-withdrawing group, it also stabilizes a negative charge in its α-position, thus allowing the umpolung of aldehydes to formyl anion equivalents. The two leading examples are the benzoin condensation and the Michael–Stetter reaction furnishing α-hydroxy ketones and 1,4-dicarbonyl compounds, which are both catalyzed by cyanides. The review also covers variants like the silyl-benzoin coupling, the aldimine coupling and the imino-Stetter reaction. Moreover, some cyanide-catalyzed heterocyclic syntheses are reviewed.1 Introduction2 Nucleophilic Additions2.1 Cyanohydrin Formation2.2 Corey–Gilman–Ganem and Related Oxidation Reactions2.3 Conjugate Addition2.4 Intramolecular Carbocyanation3 Transacylation Reactions3.1 Ester Hydrolysis and Transesterification3.2 Formation of Amides3.3 Ketones from Esters3.4 Esters from Ketones4 Transformations Involving an Umpolung4.1 Benzoin Condensation4.2 Aldimine Coupling4.3 Michael–Stetter Reaction4.4 Imino-Stetter Reaction5 Formation of Heterocycles5.1 Oxazolines from Isocyanoacetates5.2 Imidazoles from TosMIC via Oxazolines5.3 Bargellini Reaction6 Conclusion

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Section: Imino-stetter Reactionmentioning

confidence: 99%

Cyanide Anions as Nucleophilic Catalysts in Organic Synthesis

Kieslich¹,

Christoffers²

2021

Synthesis

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“…Generally, this group effectively performed the total synthesis of rac-goniomitine (rac-302) from known starting precursors with the moderate total yields (47% total yields) (Scheme 69). [154] On the other hand, this group tried to produce (+)-goniomitine 302. Asymmetric total synthesis of (+)-goniomitine 302 was started from compound 303, that after three steps gave chiral α,β-unsaturated aldehyde 298.…”

Section: Hirota and Co-workers In Isolated Tetrapetalones Frommentioning

confidence: 99%

“…Generally, this group effectively performed the total synthesis of rac ‐goniomitine ( rac ‐ 302 ) from known starting precursors with the moderate total yields (47% total yields) (Scheme 69). [154] …”

Section: Application Of Stetter Reaction In Total Synthesis Of Naturamentioning

confidence: 99%

“…Finally, upon three steps, (+)‐goniomitine (+)‐ 302 was synthesized in 46% overall yield with good ee s (84% ee ) (Scheme 70). [154] …”

Section: Application Of Stetter Reaction In Total Synthesis Of Naturamentioning

confidence: 99%

“…Significantly, since the enantiomers of goniomitine show various activities in different cancer cell lines, diverse asymmetric total synthesis of this natural product have been demonstrated [153] . Short total synthesis of rac ‐ and (+)‐goniomitine 302 was accomplished in 2019 by Cheon and co‐worker [154] . Total synthesis of rac ‐Goniomitine ( rac ‐ 302 ) was started from the condensation between 2‐aminocinnamic acid derivative 299 and rac ‐ α , β‐ unsaturated aldehyde 298 with a Dean‐Stark condenser.…”

Section: Application Of Stetter Reaction In Total Synthesis Of Naturamentioning

confidence: 99%

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Recent Advances in Stetter Reaction and Related Chemistry: An update

et al. 2020

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The Stetter reaction is actually a special CÀ C bond forming reaction through a 1,4-addition reaction in the presence of nucleophilic catalyst. It involves a reaction between aldehydes and Michael acceptors catalyzed by Nheterocyclic carbenes (NHC's) leading to preparation of 1,4dicarbonyl compounds via carbon-carbon bond formation. It offers a powerful approach to access 1,4-dicarbonyl compounds which are significant starting materials and inter-mediates in the synthesis of several heterocyclic systems, and bioactive heterocyclic framework which are present in natural products. In this review we try to underscore the recent advances in Stetter reaction and its applications from 2015 till date. Notably, we focused on the applications of Stetter reaction in the synthesis of various heterocyclic systems and total synthesis of natural products, which have largely been overlooked, previously.

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Synthesis of 2‐Substituted Tryptamines via Cyanide‐Catalyzed Imino‐Stetter Reaction

Kim

Cheon

2020

Asian J Org Chem

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Herein, we describe the development of a twostep protocol for the synthesis of 2-substituted tryptamine derivatives from 2-aminocinnamyl nitriles and aldehydes. The cyanide-catalyzed imino-Stetter reaction of 2-aminocinnamyl nitriles and aldehydes provided 2-substituted indole-3-acetonitrile derivatives. Subsequent reduction of the nitrile group afforded the desired 2-substituted tryptamine derivatives. The utility of this protocol was demonstrated in the synthesis of a potential inhibitor of 15lipoxygenase. Furthermore, the resulting 2-substituted indole-3-acetonitriles were converted to several 2,3-disubstituted indole derivatives upon transformation of the nitrile group into other functional groups.

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Total Syntheses of rac‐ and (+)‐Goniomitine

Cited by 14 publications

References 31 publications

Cyanide Anions as Nucleophilic Catalysts in Organic Synthesis

Cyanide Anions as Nucleophilic Catalysts in Organic Synthesis

Recent Advances in Stetter Reaction and Related Chemistry: An update

Synthesis of 2‐Substituted Tryptamines via Cyanide‐Catalyzed Imino‐Stetter Reaction

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