Totalsynthese von Nosiheptid

Wojtas, K. Philip; Riedrich, Matthias; Lu, Jin‐Yong; Winter, Philipp; Winkler, Thomas; Walter, Sophia; Arndt, Hans‐Dieter

doi:10.1002/ange.201603140

Angewandte Chemie

2016

DOI: 10.1002/ange.201603140

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Totalsynthese von Nosiheptid

K. Philip Wojtas

Matthias Riedrich

Jin‐Yong Lu

et al.

Abstract: Eine Totalsynthese des bismakrocyclischen Thiopeptidantibiotikums Nosiheptid gelang durch den Aufbau einer voll funktionalisierten linearen Vorstufe und konsekutive Makrocyclisierungen. Schlüsselmerkmale waren eine kritische Makrothiolactonisierung und eine milde Entschützungsstrategie für den 3‐Hydroxypyridin‐Kern. Der Naturstoff war mit isoliertem authentischem Material im Hinblick auf spektroskopische Daten und antimikrobielle Aktivität identisch.

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Cited by 4 publications

References 150 publications

(140 reference statements)

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Regioselective Functionalization of 3‐Hydroxy‐pyridine Carboxylates by Neighboring Group Assistance

Wojtas

Krahn

et al. 2016

Chemistry An Asian Journal

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Regioselective hydrolysis, transesterification, and aminolysis of unactivated, highly substituted pyridine esters were realized under mild conditions by employing neighboring group assisted catalysis. Excellent yields were achieved without active removal of the alcohol byproduct. Regioselective aminolysis had a considerable substrate scope ([hetero]aryl, alkyl and amino acid). A mechanism involving assistance by the deprotonated phenolic OH-group is suggested for hydrolysis and transesterification.

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Regioselective Functionalization of 3‐Hydroxy‐pyridine Carboxylates by Neighboring Group Assistance

Wojtas

Krahn

et al. 2016

Chemistry An Asian Journal

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Metal‐Free, Site‐Selective Peptide Modification by Conversion of “Customizable” Units into β‐Substituted Dehydroamino Acids

Saavedra

Hernández

Boto

2017

Chemistry A European J

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Our site-selective modification of serine or threonine units in peptides allows the generation of β-substituted dehydroamino acids, which increase peptide resistance to hydrolysis and may improve their biological properties. Both the terminal and internal positions can be modified, and different customizable units can be activated separately. Remarkably, high Z selectivity is achieved, even at internal positions. The conversion involves a one-pot oxidative radical scission/phosphorylation process by using the low-toxicity (diacetoxyiodo)benzene/iodine system as the scission reagent. The resulting α-amino phosphonates undergo a Horner-Wadsworth-Emmons reaction to produce the dehydroamino acid derivatives (in a Z/E ratio of usually >98:2) under mild and metal-free conditions.

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Biomimetic Synthesis of Urukthapelstatin A by Aza‐Wittig Ring Contraction

et al. 2016

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Marine bacteria produce highly cytotoxic polyheterocyclic cyclopeptide natural products by ribosomal peptide biosynthesis. Among them, urukthapelstatin A features a chain of five 2,4′‐connected azole rings within a cyclo‐octapeptide framework. We report a novel synthesis design that uses only α‐amino acids as starting materials that leads to an efficient and stereoselective total synthesis of urukthapelstatin A. Kinetically favored macro‐thiolactonization and high‐yielding aza‐Wittig heterocyclization to contract the macrocycle were crucial for success. These investigations additionally uncovered the unsuspected configurational lability of the embedded enamide substructure in solution.

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Totalsynthese von Nosiheptid

Cited by 4 publications

References 150 publications

Regioselective Functionalization of 3‐Hydroxy‐pyridine Carboxylates by Neighboring Group Assistance

Regioselective Functionalization of 3‐Hydroxy‐pyridine Carboxylates by Neighboring Group Assistance

Metal‐Free, Site‐Selective Peptide Modification by Conversion of “Customizable” Units into β‐Substituted Dehydroamino Acids

Biomimetic Synthesis of Urukthapelstatin A by Aza‐Wittig Ring Contraction

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