Total Synthesis of NW-G01, a Cyclic Hexapeptide Antibiotic, and 34-epi-NW-G01

Shibahara, Setsuya; Matsubara, Takaaki; Takahashi, Keisuke; Ishihara, Jun; Hatakeyama, Susumi

doi:10.1021/ol201912w

Cited by 25 publications

(18 citation statements)

References 23 publications

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“…In addition to the total syntheses presented in this review, we also achieved the syntheses of a variety of biologically active natural products with structural challenges such as febrifugine, 114) viridiofungin A, 115) trachyspic acid, 116) cinatrin C 1 , 117) β-erythroidine, 118) NW-G01, 119) inthomycins A-C, 120) englerin A, 121) ophiodilactones A and B, 122) and marinomycin A. 123) The strategies and methodologies we have developed are of great potential value in synthetic organic chemistry as well as pharmaceutical research.…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis of Biologically Active Natural Products Based on Highly Selective Synthetic Methodologies

Hatakeyama

2014

CHEMICAL & PHARMACEUTICAL BULLETIN

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Total syntheses of structurally and biologically intriguing natural products relying on new synthetic methodologies are described. This article features cinchona alkaloid-catalyzed asymmetric Morita-BaylisHillman reactions, heterocycle syntheses based on rhodium-catalyzed C-H amination and indium-catalyzed Conia-ene reactions, and their utilization for the syntheses of the phoslactomycin family of antibiotics, glutamate receptor agonists and antagonists, and alkaloids with characteristic highly substituted pyrrolidinone core structures.

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Section: Resultsmentioning

confidence: 99%

Total Synthesis of Biologically Active Natural Products Based on Highly Selective Synthetic Methodologies

Hatakeyama

2014

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…HPIC group are a highly versatile set of compounds that represent promising lead structures for further development as commercial agents in agriculture and medicine. 16 Some of them feature a syn-cis-stereochemistry, such as brevianamide E (6), 17 protubonine A, 18 omphalotins B, C, and D (nematicidal), 19 NW-G01 (antibiotic), 20 the complex dimeric cyclohexapeptide himastatin (7) (antibiotic) 21 and chloptosin (potent apoptosis-inducing) ( Figure 2). 22 Some possess an anti-cis-HO-HPIC moiety as exemplified by the okaramines [cf.…”

Section: Account Synlettmentioning

confidence: 99%

Procedure-Economical, Enantioselective Total Syntheses of Polycyclic Natural Products and Analogues Containing a 3a-Hydroxyhexahydropyrrolo[2,3-b]indole-2-carboxylic Acid Residue

Huang

2020

Synlett

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The 3a-hydroxyhexahydropyrrolo[2,3-b]indole-2-carboxylic acid (HPIC) residue and its aza-analogue are found in many bioactive natural products. In this account, short divergent total syntheses of several such natural products, diastereomers and analogues are described. It is demonstrated that by appropriate combination of different efficient tactics such as biomimetic/bio-inspired synthesis, chemo/regioselective reactions, umpolung of regioselectivity and/or reactivity, and tandem reactions, the enantioselective syntheses of polycyclic molecules such as (+)-asperlicin E and (–)-robustanoids A and B can be achieved in a protecting-group-free and redox-economical manner, in only three to four steps starting from l-tryptophan.1 Introduction2 Strategic Considerations2.1 Occurrence of HO-HPIC and HO-aza-HPIC Residues in Natural Products2.2 Biosyntheses of HO-HPIC and HO-aza-HPIC Residues2.3 Chemical Syntheses of HO-HPIC and HO-aza-HPIC Residues3 Procedure-Economical Syntheses of HO-HPIC-Containing Natural Products3.1 Protecting-Group-Free Syntheses of Asperlicin E, Its Diastereomer, and an Analogue3.2 Divergent Syntheses of (–)-Robustanoids A and B, a Diastereomer, and Analogues4 Conclusion and Future Perspectives

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“…[79][80][81] The selenocyclization reaction afforded the indicated kinetically favoured exo isomer with high diastereo control. Recently, Leyet al 82 employed such reaction in the total synthesis of Chloptosin, a structurally challenging anticancer agent isolated from culture broth of Streptomyces, and Hatakeyamaet al 83 in the synthesis of the cyclic hexapeptide antibiotic NW-G01 from fermentation broth of Streptomyces alboflavus. In both cases, the hydroxylated heterocyclic core, typical of the aforementioned alkaloids, was obtained under mild conditions by oxidative deselenylation with wet m-CPBA in the presence of K2CO3.…”

Section: Scheme 19 Synthesis Of Bicyclic Hydantoinsmentioning

confidence: 99%

Recent advances in selenium promoted or catalyzed electrophilic aminations of alkenes and alkynes

Palomba¹,

Mangiavacchi²,

Marini³

2019

Arkivoc

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In the last decades, synthetic methods for the construction of carbon-nitrogen bonds rapidly grew, due to the important applications of amino compounds in fine chemicals, biological and pharmaceutical sciences. The aminoselenylations of alkenes and alkynes are versatile reactions that usually occur with high regio-and stereo-control under mild reaction conditions. Linear and cyclic compounds can be prepared with wide functional and structural diversity using stoichiometric or catalytic amounts of electrophilic selenium reagents. This review collects recent advances in this attractive and fruitful research field.

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Total Synthesis of NW-G01, a Cyclic Hexapeptide Antibiotic, and 34-epi-NW-G01

Abstract: NW-G01, a cyclic hexapeptide antibiotic, and 34-epi-NW-G01 were synthesized by the highly stereoselective convergent approach for the first time, thereby unambiguously determining the absolute structure of NW-G01.

Cited by 25 publications

References 23 publications

Total Synthesis of Biologically Active Natural Products Based on Highly Selective Synthetic Methodologies

Total Synthesis of Biologically Active Natural Products Based on Highly Selective Synthetic Methodologies

Procedure-Economical, Enantioselective Total Syntheses of Polycyclic Natural Products and Analogues Containing a 3a-Hydroxyhexahydropyrrolo[2,3-b]indole-2-carboxylic Acid Residue

Recent advances in selenium promoted or catalyzed electrophilic aminations of alkenes and alkynes

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