Synthetic studies on lemonomycin: construction of the tetracyclic core

Jiménez-Somarribas, Alberto; Williams, Robert M.

doi:10.1016/j.tet.2013.05.009

Cited by 8 publications

(5 citation statements)

References 27 publications

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“…8 Finally, Losartan was obtained after the simultaneous deprotection of the N-benzyl group and reduction of the formyl group of 7 under 1 atm H 2 atmosphere in the presence of 10% Pd/C. 9 In summary, we have developed the first example of tetrazole-directed, Pd(II)-catalyzed C-H arylation. Excellent mono-/di-selectivity was achieved through adjustment of the protecting site on the tetrazole ring.…”

Section: ) Careful Examination Ofmentioning

confidence: 99%

Pd(ii)-catalyzed, controllable C–H mono-/diarylation of aryl tetrazoles: concise synthesis of Losartan

Ding

Dai

et al. 2015

Org. Biomol. Chem.

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Section: ) Careful Examination Ofmentioning

confidence: 99%

Pd(ii)-catalyzed, controllable C–H mono-/diarylation of aryl tetrazoles: concise synthesis of Losartan

Ding

Dai

et al. 2015

Org. Biomol. Chem.

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“…Williams and co-workers transformed N -acylated isoquinoline 93 into the tetracyclic core of lemonomycin 96 through an intermediate iminium ion 94 , formed by acid-catalyzed cyclization of 93 . Treatment of 94 with tert -butyl acrylate afforded tetracyclic ester 95 as a 2.4:1 mixture, which was subjected to deacetylation, epimerization, and reduction followed by removal of N , O -protecting groups supplied the lemonomycin precursor 96 (Scheme ).…”

Section: Pictet–spengler Cyclizationmentioning

confidence: 99%

Asymmetric Synthesis of Isoquinoline Alkaloids: 2004–2015

2016

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In the past decade, the asymmetric synthesis of chiral nonracemic isoquinoline alkaloids, a family of natural products showing a wide range of structural diversity and biological and pharmaceutical activity, has been based either on continuation or improvement of known traditional methods or on new, recently developed, strategies. Both diastereoselective and enantioselective catalytic methods have been applied. This review describes the stereochemically modified traditional syntheses (the Pictet-Spengler, the Bischler-Napieralski, and the Pomeranz-Fritsch-Bobbitt) along with strategies based on closing of the nitrogen-containing ring B of the isoquinoline core by the formation of bonds between C-N, N-C, C-N/N-C, and C-N/C-C atoms. Methods involving introduction of substituents at the C1 carbon of isoquinoline core along with syntheses applying various biocatalytic techniques have also been reviewed.

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“…The latest effort devoted to the synthesis of LMM was reported in 2013 by Williams and coworkers [56]. They devised a 1,3-dipolar cycloaddition of functionalized oxidopyrazinium at a late stage of synthesis (Scheme 21).…”

Section: Scheme 17mentioning

confidence: 99%

Potent Antibiotic Lemonomycin: A Glimpse of Its Discovery, Origin, and Chemical Synthesis

et al. 2022

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Lemonomycin (1) was first isolated from the fermentation broth of Streptomyces candidus in 1964. The complete chemical structure was not elucidated until 2000 with extensive spectroscopic analysis. Lemonomycin is currently known as the only glycosylated tetrahydroisoquinoline antibiotic. Its potent antibacterial activity against Staphylococcus aureus and Bacillus subtilis and complex architecture make it an ideal target for total synthesis. In this short review, we summarize the research status of lemonomycin for biological activity, biosynthesis, and chemical synthesis. The unique deoxy aminosugar-lemonose was proposed to play a crucial role in biological activity, as shown in other antibiotics, such as arimetamycin A, nocathiacin I, glycothiohexide α, and thiazamycins. Given the self-resistance of the original bacterial host, the integration of biosynthesis and chemical synthesis to pursue efficient synthesis and further derivatization is in high demand for the development of novel antibiotics to combat antibiotic-resistant infections.

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Synthetic studies on lemonomycin: construction of the tetracyclic core

Cited by 8 publications

References 27 publications

Pd(ii)-catalyzed, controllable C–H mono-/diarylation of aryl tetrazoles: concise synthesis of Losartan

Pd(ii)-catalyzed, controllable C–H mono-/diarylation of aryl tetrazoles: concise synthesis of Losartan

Asymmetric Synthesis of Isoquinoline Alkaloids: 2004–2015

Potent Antibiotic Lemonomycin: A Glimpse of Its Discovery, Origin, and Chemical Synthesis

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