Studies toward the Total Synthesis of the Marine Macrolide Salarin C

Schrof, Raffael; Altmann, Karl‐Heinz

doi:10.1021/acs.orglett.8b03422

Cited by 12 publications

(23 citation statements)

References 35 publications

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“…Aureol B (58) exhibited modest cytotoxic activity against K562 cell line with IC 50 value of 4.8 mM where, melemeleone C (56) exhibited modest activity against A549 cell line with IC 50 value of 4.2 mM. Other meroterpenoids (57,(59)(60)(61) showed signicant cytotoxicity against the two cell lines with range of (0.7-4.9 mM) 36 Fig. 6.…”

Section: Potent Bioactive Compounds Isolated From Dictyoceratida Sponmentioning

confidence: 98%

“…All macrocyclic intermediates during the synthesis were found to be of limited stability. 61 Also, the synthesis of the macrocyclic core of salarin C was described using two epoxides being replaced by alkene moieties. In the key step, ring-closing metathesis exclusively afforded the (E)-product.…”

Section: Potent Bioactive Compounds Isolated From Family Spongiidaementioning

confidence: 99%

“…Structures of compounds(53)(54)(55)(56)(57)(58)(59)(60)(61).34966 | RSC Adv., 2020, 10,34959-34976 This journal is © The Royal Society of Chemistry 2020 RSC Advances Review Open Access Article. Published on 21 September 2020.…”

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confidence: 99%

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Marine natural products from sponges (Porifera) of the order Dictyoceratida (2013 to 2019); a promising source for drug discovery

et al. 2020

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Section: Potent Bioactive Compounds Isolated From Dictyoceratida Sponmentioning

confidence: 98%

Section: Potent Bioactive Compounds Isolated From Family Spongiidaementioning

confidence: 99%

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Marine natural products from sponges (Porifera) of the order Dictyoceratida (2013 to 2019); a promising source for drug discovery

et al. 2020

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“…245.1883. (R)-Pentadec-1-yn-3-ol(31).To a solution of compound 3.26 (400 mg, 1.8 mmol) in dry isopropyl alcohol (7.2 mL), Noyori transfer hydrogen catalyst (Ru-R,R-catalyst) (95 mg, 0.15 mmol) was added at 0 °C. The reaction mixture was then allowed to warm at room temperaturePaperOrganic & Biomolecular Chemistry and stirred for 3 h at the same temperature.…”

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confidence: 99%

Synthetic studies towards naturally occurring γ-(Z)/(E)-alkylidenebutenolides through bimetallic cascade cyclization and an adventitious photoisomerization method

et al. 2022

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“…In the synthesis of dideoxysalarin C recently reported by Altmann and Schrof, the desired macrocycle 433 was constructed under Shina conditions with only about 7% of isomerised (2E, 4E)dienoate byproduct observed based on 1 H NMR analysis. 305 Scheme 3.25 Shiina reaction towards the synthesis of dideoxysalarin C. 305 Interestingly, in the synthesis of an analogue of dictyostatin, the Shinna reaction on secoacid 435 provided a 60/40 ratio of Z,E-product 436 and E,E-product 437 (Scheme…”

Section: Scheme 322mentioning

confidence: 99%

Towards Synthesis of Simplified Analogues of Pateamine A

Xu¹

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<p>Pateamine A (22) is a natural product that was isolated from a marine sponge inhabiting the coast of New Zealand. It exhibits potent inhibition of protein synthesis and nonsense-mediated mRNA decay through binding with eIF4A isoforms. Due to the scarcity of pateamine A (22) in the natural source and the low yield of total synthesis of pateamine A, it is necessary to prepare structurally simplified analogues which would allow further research on structure-activity relationships (SAR) of pateamine A (22). Based on the structure-activity relationship studies reported by Romo and co-workers, a simplified triazole analogue 182 lacking methyl groups was synthesized by Hemi Cumming, a previous Ph.D. student who studied at Victoria University of Wellington. The antiproliferative activity of this analogue was found to be significantly lower than that of pateamine A, suggesting that the thiazole embedded within the molecule or the excised methyl groups are crucial for its potency. Therefore, to further explore the necessary features for its selective activity for eIF4A isoforms, new thiazole analogues 183 – 186 and triazole analogues (10S)-and (10R)-analogue 187 were targeted in this project. The preparation of the thiazole-containing macrocyclic core of analogues 183 and 184 was achieved. It features: (1) gold-catalysed thiazole formation through coupling between an alkyne fragment and a thioamide fragment; (2) preparation of the Z,E-dienoate moiety by base-induced ring-opening of a δ-substituted-α, β-unsaturated lactone; and (3) a modified Mukaiyama macrolactonisation. The synthesis of the triazole-containing macrocyclic core of (10S)-analogue 187 was completed. It features: (1) a copper-catalysed triazole formation through 1,3-dipolar cycloaddition between an alkyne fragment and an azide fragment; (2) preparation of the Z,E-dienoate moiety by base-induced ring-opening of δ-substituted-α, β-unsaturated lactone; and (3) a modified Mukaiyama macrolactonisation. Studies on the preparation of a side-chain fragment with suitable functionalities to allow coupling with the various macrocycles through olefination reactions were also conducted. The attachment of the side-chain fragment onto the macrocyclic cores for the synthesis of the targeted analogues 183 and 184 and (10S)-analogue 187 will be investigated in future work. These experimental results will inform the synthesis of new generation analogues to further study the key structures required for effective binding to the protein target eIF4A and selectivity between isoforms.</p>

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Studies toward the Total Synthesis of the Marine Macrolide Salarin C

Cited by 12 publications

References 35 publications

Marine natural products from sponges (Porifera) of the order Dictyoceratida (2013 to 2019); a promising source for drug discovery

Marine natural products from sponges (Porifera) of the order Dictyoceratida (2013 to 2019); a promising source for drug discovery

Synthetic studies towards naturally occurring γ-(Z)/(E)-alkylidenebutenolides through bimetallic cascade cyclization and an adventitious photoisomerization method

Towards Synthesis of Simplified Analogues of Pateamine A

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