First Total Synthesis of the Potent Anticancer Natural Product Dideoxypetrosynol A: Preparation of the “Skipped” (<i>Z</i>)‐Enediyne Moiety by Oxidative Coupling of Homopropargylphosphonium Ylide

Gung, Benjamin W.; Omollo, Ann O.

doi:10.1002/ejoc.200800593

Cited by 11 publications

(7 citation statements)

References 30 publications

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“…), 343 isolated as a racemic mixture, were synthesised separately. 344 An enantiospecific synthesis of bitungolide F (Theonella swinhoei) 345 established the absolute configuration. 346 Plakortis angulospiculatus (Baı ´a de Todos os Santos, Bahia, Brazil) yielded the cyclic peroxide plakortenone 331.…”

Section: Green Algaementioning

confidence: 99%

Marine natural products

et al. 2010

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This review covers the literature published in 2008 for marine natural products, with 829 citations (613 for the period January to December 2008) referring to compounds isolated from marine microorganisms and phytoplankton, green algae, brown algae, red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1065 for 2008), 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: Green Algaementioning

confidence: 99%

Marine natural products

et al. 2010

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“…[12] As imilara pproache mploying Lipase AK (Amano)w as later used to access( S)-eicos-(4E)-en-1-yn-3-ol (1), [13] both enantiomers of the two-headed compounds adociacetylene, [14] and duryne, [15] and (S,S)-dideoxypetrosynol. [16] Lipase PS (Amano) was also reported to catalyzea nR-selective acetylation, exploited for the synthesis and absolute configurationdetermination of an ew two-headed cytotoxic metabolite from the marine sponge Petrosia sp. (4E,24E)-14-methyloctacosa-4,24diene-1,27-diyne-3,26-diol.…”

Section: Enzymatic Kinetic Resolutionmentioning

confidence: 99%

Skeletal Optimization of Cytotoxic Lipidic Dialkynylcarbinols

et al. 2018

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In line with a recent study of the pharmacological potential of bioinspired synthetic acetylenic lipids, after identification of the terminal dialkynylcarbinol (DAC) and butadiynyl alkynylcarbinol (BAC) moieties as functional antitumor pharmacophoric units, this work specifically addresses the issue of carbon backbone length. A systematic variation of the aliphatic chain length was thus carried out in both the DAC and BAC series. The critical impact of the length of the lipidic skeleton was first confirmed in the racemic series, with the highest cytotoxic activity observed for C to C backbones. Enantiomerically enriched samples were prepared by asymmetric synthesis of the optimal C DAC and C BAC derivatives. Samples with upgraded enantiomeric purity were alternatively produced by enzymatic kinetic resolution. Eutomers possessing the S configuration displayed cytotoxicity IC values as low as 15 nm against HCT116 cancer cells, the highest level of activity reached to date in this series.

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“…Recently, we completed the total syntheses of several polyacetylenic natural products including adociacetylene, minquartynoic acids, bidensyneosides, duryne, and dideoxypetrosynol. [16][17][18][19][20][21] On the basis of our experience in this area, we planned our first attempt by using known compounds 4 and 6 to construct the extended conjugation system as shown in Scheme 1.…”

Section: Resultsmentioning

confidence: 99%

A Concise Synthesis of R‐(–)‐Cicutoxin, a Natural 17‐Carbon Polyenyne

Gung¹,

Omollo²

2009

Eur J Org Chem

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A concise synthesis of the natural polyenyne R-(−)-cicutoxin (1) is described. After several trials, the successful synthesis commenced with three key fragments, R-(−)-1-hexyn-3-ol (8), 1,4-diiodo-1,3-butadiene (9), and the THP protected 4,6-heptadiyn-1-ol (6). Sonogashira coupling of compound 9 with acetylenes 6 and 8 gave the 17-carbon frame, which upon regio-selective reduction of a triple bond with red Al and removal of the THP protecting group afforded the natural product in four linear steps. The triply convergent synthesis gave R-(−)-cicutoxin in 18% overall yield.

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First Total Synthesis of the Potent Anticancer Natural Product Dideoxypetrosynol A: Preparation of the “Skipped” (Z)‐Enediyne Moiety by Oxidative Coupling of Homopropargylphosphonium Ylide

Cited by 11 publications

References 30 publications

Marine natural products

Marine natural products

Skeletal Optimization of Cytotoxic Lipidic Dialkynylcarbinols

A Concise Synthesis of R‐(–)‐Cicutoxin, a Natural 17‐Carbon Polyenyne

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