Further Study toward Amipurimycin:  Synthesis of the Northern Part

Czernecki, S.; Franco, Santiago; Valéry, Jean‐Marc

doi:10.1021/jo962266n

Cited by 24 publications

(10 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Tremendous efforts toward the chemical synthesis of amipurimycin are described . Thus, a number of the advanced precursors and analogues of amipurimycin have been synthesized, including a thymine analogue by Datta et al., a linear analogue by Czernecki et al., peptidyl glycoside fragments by Garner et al., and thymine nucleoside fragments by Dhavale et al . However, none of those synthetic approaches could lead to the target amipurimycin.…”

Section: Figurementioning

confidence: 99%

Amipurimycin: Total Synthesis of the Proposed Structures and Diastereoisomers

et al. 2018

View full text Add to dashboard Cite

The proposed diastereoisomers (1 a-d) together with their C8'-epimers (1 e-h) of amipurimycin, a unique antifungal peptidyl nucleoside antibiotic, have been synthesized for the first time. The synthetic approach is efficient and stereodivergent, and features a stereoselective aldol condensation to build the branched C9 sugar amino acid skeleton and a regio- and stereocontrolled gold(I)-catalyzed N-glycosylation to furnish the purine nucleoside. Analysis of the NMR data suggests that the previously assigned configuration of the tertiary C3' in amipurimycin should be of opposite configuration.

show abstract

Section: Figurementioning

confidence: 99%

Amipurimycin: Total Synthesis of the Proposed Structures and Diastereoisomers

et al. 2018

View full text Add to dashboard Cite

show abstract

“…The structural features, as well as the uncharacterized mechanism of antifungal action, render APM an attractive yet challenging target for synthesis. In the past three decades, various structural fragments and analogues have been synthesized. − However, the true configuration of APM was not resolved until a recent work on total synthesis of eight diastereoisomers, where the authors suggested that the configuration previously assigned at C-3′ should be opposite . The challenges in total synthesis of APM have also raised interest in its biosynthesis.…”

mentioning

confidence: 99%

Identification of the Amipurimycin Gene Cluster Yields Insight into the Biosynthesis of C9 Sugar Nucleoside Antibiotics

et al. 2019

View full text Add to dashboard Cite

Feeding studies indicate a possible synthetic pattern for the N-terminal cis-aminocyclopentane carboxylic acid (ACPC) and suggest an unusual source of the highcarbon sugar skeleton of amipurimycin (APM). The biosynthetic gene cluster of APM was identified and confirmed by in vivo experiments. A C9 core intermediate was discovered from null mutants of ACPC pathway, and an ATP-grasp enzyme (ApmA8) was reconstituted in vitro for ACPC loading. Our observations allow a first proposal of the APM biosynthetic pathway. Letter pubs.acs.org/OrgLett

show abstract

“…Desilylation with tetrabutylammonium fluoride in anhydrous THF, followed by acetylation (Ac 2 O, Py) of the N -hydroxy group, afforded compound 4 in 88% purified yield. The ethynyl group was oxidized according to the method of Czernecki. 2h, Unfortunately, the use of sodium bicarbonate in the reaction medium results in the loss of the acetyl group . In addition, workup with sodium bisulfite gave a complex mixture from which we could not identify optimal conditions for purifying the desired carboxylic acid.…”

mentioning

confidence: 99%