Enantiospecific first total synthesis of 7a(S)-p-hydroxyphenopyrrozin

Kothapalli, Yugandhar; Puthukanoori, Ravi Kumar; Alapati, Srinivasa Rao

doi:10.1016/j.tetlet.2012.01.098

Cited by 10 publications

(6 citation statements)

References 8 publications

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“…(sediment, Gulf of Mexico), 400 has been synthesised in an enantiospecic manner from L-proline utilising base-mediated cyclisation and oxygenation as key steps. 401 An improved method for the sulfenylation of 2,5-diketopiperazines utilising alkali metal hexamethyldisilazide bases has been employed in the synthesis of gliotoxin G, 258 a metabolite of the marine fungus Penicillium sp. 402 Balticolid, a 12-membered macrolide, originally isolated from an Ascomycetous fungus separated from driwood, 403 has been synthesised utilising a Hoveyda-Grubbs II catalyst assisted ring-closing metathesis.…”

Section: Synthetic Aspectsmentioning

confidence: 99%

Marine natural products

et al. 2014

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This review covers the literature published in 2012 for marine natural products, with 1035 citations (673 for the period January to December 2012) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1241 for 2012), together with the relevant biological activities, source organisms and country of origin. Biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.

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Section: Synthetic Aspectsmentioning

confidence: 99%

Marine natural products

et al. 2014

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“…However, two chemical syntheses for p-hydroxyphenopyrrozin were reported. The first starts from l-proline and requires 11 steps to obtain a 5.8% yield of p-hydroxyphenopyrrozin [74], while the second makes use of a three-step condensation cyclization of α-oxoesters and cyclic imines, resulting in an overall yield of 55% [75].…”

Section: Pyrrolizidinesmentioning

confidence: 99%

Alkaloids from Marine Fungi: Promising Antimicrobials

et al. 2020

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Resistance of pathogenic microorganisms against antimicrobials is a major threat to contemporary human society. It necessitates a perpetual influx of novel antimicrobial compounds. More specifically, Gram− pathogens emerged as the most exigent danger. In our continuing quest to search for novel antimicrobial molecules, alkaloids from marine fungi show great promise. However, current reports of such newly discovered alkaloids are often limited to cytotoxicity studies and, moreover, neglect to discuss the enigma of their biosynthesis. Yet, the latter is often a prerequisite to make them available through sufficiently efficient processes. This review aims to summarize novel alkaloids with promising antimicrobial properties discovered in the past five years and produced by marine fungi. Several discovery strategies are summarized, and knowledge gaps in biochemical production routes are identified. Finally, links between the structure of the newly discovered molecules and their activity are proposed. Since 2015, a total of 35 new antimicrobial alkaloids from marine fungi were identified, of which 22 showed an antibacterial activity against Gram− microorganisms. Eight of them can be classified as narrow-spectrum Gram− antibiotics. Despite this promising ratio of novel alkaloids active against Gram− microorganisms, the number of newly discovered antimicrobial alkaloids is low, due to the narrow spectrum of discovery protocols that are used and the fact that antimicrobial properties of newly discovered alkaloids are barely characterized. Alternatives are proposed in this review. In conclusion, this review summarizes novel findings on antimicrobial alkaloids from marine fungi, shows their potential as promising therapeutic candidates, and hints on how to further improve this potential.

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“…This route provided PAs from the hyacinthacine family 120,152-162 as well as absouline, [163][164][165] isoretronecanol, 166,167 pyrrolam A, 168,169 trachelanthamidine, 170,171 casuarine, 158,172,173 heliotridane, 175 turneforcidine 175 and a fungi PA -7a(S)-phydroxyphenopyrrozin. 176 Typical yields for the cyclization step were in the range from 22% to quantitative. A slightly modified lactamization process relying on the use of hexahydropyrrolo[1,2-b]isoxazole as a starting material (product of a nitrone cycloadditon) was demonstrated by Goti and co-workers recently.…”

Section: Lactamizationmentioning

confidence: 99%