A Short and Efficient Synthesis of (2S,3S,4S)-tert-Butyl 3,4-Dihydroxy-2-(methoxymethyl)-5-oxopyrrolidine-1-carboxylate

Passiniemi, Mikko; Koskinen, Ari M. P.

doi:10.1055/s-0029-1218843

Cited by 6 publications

(10 citation statements)

References 7 publications

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“…Installation of the C-2 stereocentre again began with Garner’s aldehyde 48 and Wittig olefination, followed by Sharpless dihydroxylation to stereoselectively afford diol 49 [59–60]. The C-2 epimer was accessed via Still–Gennari olefination of aldehyde 48 to afford the Z-olefin, which underwent dihydroxylation using potassium osmate to afford diol 50 [61–62]. With both diastereomers in hand, conversion to protected amino acids 46 and 47 was effected in four steps.…”

Section: Reviewmentioning

confidence: 99%

Enduracididine, a rare amino acid component of peptide antibiotics: Natural products and synthesis

Atkinson¹,

Naysmith²,

Furkert³

et al. 2016

Beilstein J. Org. Chem.

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Rising resistance to current clinical antibacterial agents is an imminent threat to global public health and highlights the demand for new lead compounds for drug discovery. One such potential lead compound, the peptide antibiotic teixobactin, was recently isolated from an uncultured bacterial source, and demonstrates remarkably high potency against a wide range of resistant pathogens without apparent development of resistance. A rare amino acid residue component of teixobactin, enduracididine, is only known to occur in a small number of natural products that also possess promising antibiotic activity. This review highlights the presence of enduracididine in natural products, its biosynthesis together with a review of analogues of enduracididine. Reported synthetic approaches to the cyclic guanidine structure of enduracididine are discussed, illustrating the challenges encountered to date in the development of efficient synthetic routes to facilitate drug discovery efforts inspired by the discovery of teixobactin.

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Section: Reviewmentioning

confidence: 99%

Enduracididine, a rare amino acid component of peptide antibiotics: Natural products and synthesis

Atkinson¹,

Naysmith²,

Furkert³

et al. 2016

Beilstein J. Org. Chem.

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“…The intermediate can be derivatized further, thus providing a route for greater molecular diversity. Diastereoselective dihydroxylation of A with OsO 4 leads to triols B , which have been utilized in the syntheses of calyculins family [83–84], D- ribo -phytosphingosine [85], and radicamine [86–87]. If the R-group in A is an ester, diastereoselective Michael addition leads to structures C [88–92].…”

Section: Reviewmentioning

confidence: 99%

“…We have been interested in the synthesis of Z -enoate 73 [84]. The Still–Gennari modification to the phosphonate makes the synthesis of Z -enoates possible [115].…”

Section: Reviewmentioning

confidence: 99%

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Garner’s aldehyde as a versatile intermediate in the synthesis of enantiopure natural products

Passiniemi¹,

Koskinen²

2013

Beilstein J. Org. Chem.

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SummarySince its introduction to the synthetic community in 1984, Garner’s aldehyde has gained substantial attention as a chiral intermediate for the synthesis of numerous amino alcohol derivatives. This review presents some of the most successful carbon chain elongation reactions, namely carbonyl alkylations and olefinations. The literature is reviewed with particular attention on understanding how to avoid the deleterious epimerization of the existing stereocenter in Garner’s aldehyde.

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“…[13d] Verseifung des Ethylesters gefolgt von einer Fischer-Veresterung bei gleichzeitiger Boc-Entschützung ergab Aminhydrochlorid 12. Um 12 mit O-methyliertem Serin 13 [17] [17] Das Boc-entschützte Aminhydrochlorid 16 wurde mit N-Boc-Phenyl-Selenocystein 17 [18] geknüpft um Tripeptid 18, als Vorläufer des nordöstlichen Fragments der Thiamyxine, in guter Ausbeute zu erhalten.…”

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Totalsynthese von Thiamyxin A–C und Thiamyxin E, potente RNA‐Virus inhibierende (Cyclo)depsipeptide

Bauer

Kazmaier

2023

Angewandte Chemie

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Wir präsentieren die erste Totalsynthese der Thiamyxine A-C und des jetzt vollständig charakterisierten Thiamyxins E, einer interessanten Klasse thiazolund thiazolinreicher Depsipeptide mit vielfältiger antiviraler Aktivität. Die Synthese zeichnet sich aus durch einen parallelen Ringschluss zu zwei Methylthiazolin-Einheiten unter geringer Epimerisierung des sehr labilen benachbarten stereogenen Zentrums. Des Weiteren wird die dreistufige Synthese einer ungewöhnlichen Hydroxysäure sowie die oxidationsfreie Eliminierung eines Phenylselenids zum Dehydroalanin gezeigt. Die Ausnutzung des säurelabilen Stereozentrums am Isoleucin-Rest und die erneute Öffnung der Makrolactone ermöglichen den Zugang zu den vier Thiamyxinen in guten Ausbeuten und Diastereomerenverhältnissen aus einem einzigen Vorläufer. Durch die modular gestaltete Totalsynthese sind weitere Bioaktivitätstests und die Erforschung eines Pharmakophors über die Synthese weiterer Derivate möglich.

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A Short and Efficient Synthesis of (2S,3S,4S)-tert-Butyl 3,4-Dihydroxy-2-(methoxymethyl)-5-oxopyrrolidine-1-carboxylate

Abstract: A short and efficient synthesis of (2S,3S,4S)-tert-butyl 3,4-dihydroxy-2-(methoxymethyl)-5-oxopyrrolidine-1-carboxylate

Cited by 6 publications

References 7 publications

Enduracididine, a rare amino acid component of peptide antibiotics: Natural products and synthesis

Enduracididine, a rare amino acid component of peptide antibiotics: Natural products and synthesis

Garner’s aldehyde as a versatile intermediate in the synthesis of enantiopure natural products

Totalsynthese von Thiamyxin A–C und Thiamyxin E, potente RNA‐Virus inhibierende (Cyclo)depsipeptide

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