Diastereoselective Synthesis of (±)-Heliotropamide by a One-Pot, Four-Component Reaction

Younai, Ashkaan; Chin, Gregory F.; Shaw, Jared T.

doi:10.1021/jo1019317

Cited by 26 publications

(33 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In addition, we have disclosed a synthesis of the natural product heliotropamide (1, Fig. 1) using this reaction to assemble the lactam core (2). In this report, we disclose methodology for the synthesis of structurally diverse γ-lactams using our previously described 4CR as a starting point.…”

mentioning

confidence: 95%

Ammonia synthons for the multicomponent assembly of complex γ-lactams

Tan

Martin

Fettinger

et al. 2011

Proc. Natl. Acad. Sci. U.S.A.

Self Cite

View full text Add to dashboard Cite

The synthesis of γ-lactams that are unsubstituted at the 1-position (nitrogen) as well as their subsequent N -functionalization is reported. A recently discovered four-component reaction (4CR) is employed with either an ammonia precursor or a protected form of ammonia that can be deprotected in a subsequent synthetic step. These methods represent the first multicomponent assembly of complex lactam structures that are unsubstituted at nitrogen. In addition, two methods for the introduction of nitrogen substituents that are not possible through the original 4CR are reported. X-ray crystallographic analysis of representative structures reveals conformational changes in the core structure that will enable future deployment of this chemistry in the design and synthesis of diverse collections of lactams suitable for the discovery of new biological probes.

show abstract

mentioning

confidence: 95%

Ammonia synthons for the multicomponent assembly of complex γ-lactams

Tan

Martin

Fettinger

et al. 2011

Proc. Natl. Acad. Sci. U.S.A.

Self Cite

View full text Add to dashboard Cite

show abstract

“…In a recent perspective article, discovery of new synthetic methods to access substituted aliphatic heterocycles stereoselectively from acyclic precursors has been listed as one of the major synthetic challenges that could contribute significantly to drug discovery . In this respect, cyclization reactions of N -acyliminium ions offer a plethora of opportunities for the synthesis of a broad range of nitrogen heterocycles. − In particular, the aza-Nazarov reaction stands out as a potentially useful transformation for the construction of five-membered, nitrogen-containing heterocyclic structures . However, whereas the catalytic, all-carbon Nazarov reaction has enjoyed remarkable advances within the past two decades, the analogous aza-Nazarov reaction is still in its infancy .…”

mentioning

confidence: 99%

Aza-Nazarov Cyclization Reactions via Anion Exchange Catalysis

et al. 2019

View full text Add to dashboard Cite

A catalytic aza-Nazarov cyclization between 3,4-dihydroisoquinolines and α,β-unsaturated acyl chlorides has been developed to access α-methylene-γ-lactam products in good yields (up to 79%) as single diastereomers. The reactions proceed efficiently when AgOTf is used as an anion exchange catalyst with a 20 mol % loading at 80°C. Computational studies were performed to investigate the reaction mechanism, and the findings support the role of the −TMS group in reducing the reaction barrier of the key cyclization step.

show abstract

“…The protection of the amino group in the tyramine was done in basic media with Boc 2 C, 6 and the diiodination of the aromatic ring with N-iodosuccinimide (NIS), 7 getting a di-halogenated compound in positions 3 and 5, obtaining compound A with a 70% yield for two steps. 1 H nuclear magnetic resonance (NMR) analysis of compound A shows a singlet at 7.50 ppm for two protons, which corresponds to hydrogen at 2, which confirm the diiodination at the ortho position of the phenyl ring.…”

Section: Chemistrymentioning

confidence: 99%

Anti-Parasite Activity of Novel 3,5-Diiodophenethyl-benzamides

Restrepo¹,

Surmay²,

Galeano³

et al. 2018

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

Novel iodotyramides with para-substituted benzoic acids were synthesized via electrophilic aromatic substitutions and amide coupling via N,N'-diisopropylcarbodiimide (DIC) in dimethylformamide (DMF). All derivatives were in vitro screened against U-937 macrophages and Plasmodium falciparum, Leishmania panamensis and Trypanosoma cruzi protozoan parasites. The hemolytic activity was evaluated on human red blood cells (RBC). -methoxyphenethyl)-4-methoxybenzamide were the most active against L. panamensis with an effective concentration 50 (EC 50 ) of 17.9 and 17.5 μg mL -1 , respectively; while compounds N- (3,5-diiodo-4-methoxyphenethyl)-4-methylbenzamide and N-(3,5-diiodo-4-methoxyphenethyl

show abstract

Diastereoselective Synthesis of (±)-Heliotropamide by a One-Pot, Four-Component Reaction

Cited by 26 publications

References 16 publications

Ammonia synthons for the multicomponent assembly of complex γ-lactams

Ammonia synthons for the multicomponent assembly of complex γ-lactams

Aza-Nazarov Cyclization Reactions via Anion Exchange Catalysis

Anti-Parasite Activity of Novel 3,5-Diiodophenethyl-benzamides

Contact Info

Product

Resources

About