Total Synthesis of Microsclerodermin E

Zhu, Jidong; Ma, Dawei

doi:10.1002/anie.200352423

Cited by 76 publications

(31 citation statements)

References 29 publications

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“…Additionally, we removed the t-butyl carbamate (referred to as Boc) group from D1 – D3 using TFA to produce D-1 . A hydrogen reduction over Pd/C [11] removed the benzyl group from D1 , D4 and D5 before amino acids protected by benzyl ester were coupled using DEPBT, generating tripeptides T1 – T5 in an 83%–88% yield. Subsequently, the benzyl group was removed to obtain T-2 .…”

Section: Resultsmentioning

confidence: 99%

Paper Synthesis, Cytotoxicity and Apoptosis Induction in Human Tumor Cells by Galaxamide and Its Analogues

et al. 2014

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Our previous study reported that galaxamide, which is a cyclo-pentapeptide containing five leucines that was extracted from Galaxaura filamentosa, displayed remarkable anticancer cytotoxicity. This novel cyclo-peptide provided a new skeleton for the structural modifications used in finding new drugs with better anticancer properties. In this study, five analogues were synthesized based on changing the number of d/l amino acids by adding a new amino acid, phenylalanine. Galaxamide and five of its analogues were evaluated through MTT assays to examine their cytotoxic activities. We found that modified analogue 5, which is referred to as A5, displayed broad spectrum cytotoxic activity toward every cell line tested; in addition, the IC50 of A5 was lower than that of galaxamide and the other analogues. Furthermore, we used flow cytometry and western blot assays to investigate whether galaxamide and A5 could induce cancer cell apoptosis. The flow cytometric studies showed that HepG2 cells treated with different concentrations of galaxamide or A5 over 72 h displayed significant and dose-dependent increases in the percentages of early-stage apoptotic cells. Western blotting revealed that both compounds induce caspase-dependent apoptosis in HepG2 cells through a mitochondria-mediated pathway. The results demonstrate that galaxamide and its analogues have potential applications as clinical anticancer drugs.

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Section: Resultsmentioning

confidence: 99%

Paper Synthesis, Cytotoxicity and Apoptosis Induction in Human Tumor Cells by Galaxamide and Its Analogues

et al. 2014

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“…Carbohydrates have been used widespread as chiral sources in asymmetric syntheses of natural products [31][32][33][34][35][36][37]. Although various carbohydrates are available, in most of them one enantiomer is natural abundant but another isomer is difficult to get in much quantity.…”

Section: The Total Syntheses Of Nanaomycin D and Kalafunginmentioning

confidence: 99%

Total syntheses of bioactive natural products from carbohydrates

Tatsuta

Hosokawa

2006

Science and Technology of Advanced Materials

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Total syntheses of bioactive natural products recently accomplished in our laboratories are described. They are classified by structures of target molecules and are focused on our original approach to their own structures. The target molecules include nanaomycin, kalafungin, BE-54238B, tetracycline, rosmarinecine, thienamycin, luminacines C 1 and C 2 , tetrodecamycin, cochleamycin A, and tubelactomicin A, which have been synthesized as optically pure form from carbohydrates.

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“…During the studies on the total synthesis of macrosclerodermin E, 10 we tried the typical procedure of Julia olefination in order to convert sulfone 1 into diene 2 adoping sodium amalgam as a reducing agent (Eq. 1).…”

Section: Introductionmentioning

confidence: 99%

Sodium Amalgam, a Useful Reducing Reagent for Formation of Amines from Azides Bearing a Variety of Functional Groups.

Xie

Zhu

et al. 2006

ChemInform

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Reduction of azides to amines without touching benzyl, t-butyldimethylsilyl, t-butyldiphenylsilyl, trityl and tetrahydropyranyl ether protecting groups, C-C double and triple bond, as well as aromatic bromide and nitrile functional groups, was achieved using sodium amalgam as a reducing reagent in methanol at temperature from -40 ℃ to room temperature. However, ester group was reduced under this condition.

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Total Synthesis of Microsclerodermin E

Cited by 76 publications

References 29 publications

Paper Synthesis, Cytotoxicity and Apoptosis Induction in Human Tumor Cells by Galaxamide and Its Analogues

Paper Synthesis, Cytotoxicity and Apoptosis Induction in Human Tumor Cells by Galaxamide and Its Analogues

Total syntheses of bioactive natural products from carbohydrates

Sodium Amalgam, a Useful Reducing Reagent for Formation of Amines from Azides Bearing a Variety of Functional Groups.

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