Total Synthesis of Mycalolides A and B through Olefin Metathesis

Kita, Masakazu; Oka, Hirotaka; Usui, Akihiro; Ishitsuka, Tomoya; Mogi, Yuzo; Watanabe, Hidekazu; Tsunoda, Masaki; Kigoshi, Hideo

doi:10.1002/anie.201507795

Cited by 32 publications

(18 citation statements)

References 58 publications

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“…The total synthesis of yaku'amide A 1108, including eight possible stereoisomers of its core region, required revision of structure, and also that of congener B 1109. 747,748 Macrolides are attractive targets for synthesis with the construction of tulearin A, 749,750 mycalolide B, 751,752 and muironolide A 1110 being completed, the latter requiring a structural revision. 753,754 Pyridines nakinadine D-F, 755,756 indoles scalaridine A, 757,758 dragmacidin D 1111, [759][760][761] dendridine A, 762,763 and guanidine batzelladine B 764,765 are alkaloid compounds that have all been synthesised.…”

Section: Spongesmentioning

confidence: 99%

Marine natural products

et al. 2017

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Covering: 2015. Previous review: Nat. Prod. Rep., 2016, 33, 382-431This review covers the literature published in 2015 for marine natural products (MNPs), with 1220 citations (792 for the period January to December 2015) 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 (1340 in 429 papers for 2015), together with the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.

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Section: Spongesmentioning

confidence: 99%

Marine natural products

et al. 2017

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“…A known primary alcohol 9 (18) prepared from ( S )-3-hydroxy-2-methylpropionate was converted into the phenyl tetrazole (PT) sulfide with aryl disulfide/ n Bu 3 P, and subsequent oxidation with meta -chloroperbenzoic acid ( m -CPBA) yielded PT–sulfone 10 . Julia–Kocienski olefination 19 of 10 with sterically hindered aldehyde 11 (4c) and lithium hexamethyldisilazide (LHMDS) as a base in 1,2-dimethoxyethane (DME) 20 at temperatures of −55 °C to room temperature afforded an olefin quantitatively ( E / Z = 1:2). Simultaneous catalytic hydrogenation of the olefin and hydrogenolysis of the benzyl group using palladium(II) hydroxide on carbon resulted in the epimerization of C29 secondary alcohol.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Biological Activities of Aplyronine A Analogues toward the Development of Antitumor Protein–Protein Interaction Inducers between Actin and Tubulin: Conjugation of the C1–C9 Macrolactone Part and the C24–C34 Side Chain

et al. 2019

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Aplyronine A (ApA) is an antitumor marine macrolide that induces an protein–protein interaction (PPI) between actin and tubulin. The C1–C9 macrolactone part including the C7 N , N , O -trimethylserine (TMSer) ester is important for its highly potent activities. To develop new antitumor PPI inducers, four aplyronine analogues were synthesized, which bear the C1–C9 macrolactone part with 0–2 TMSer ester(s) and the C24–C34 actin-binding side chain. Despite exhibiting potent actin-depolymerizing activity comparable to that of ApA, these analogues did not show potent cytotoxicity or depolymerize microtubules. Molecular modeling studies suggested that the whole macrolactone moiety of aplyronines was important to fix the conformation of the C7 TMSer ester moiety, while the linear C1–C9 part was insufficient. Still, our study newly proposed that fixed conformations of the C7 or C9 TMSer esters in aplyronines that protrude from the actin surface are important for binding to tubulin and inhibit microtubule dynamics.

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“…Its polyketide chain contains eight of the eleven stereogenic centers present in this compound. Only two total syntheses and two polypropionate fragments have been reported to date [51–53]. …”

Section: Resultsmentioning

confidence: 99%

Reiterative epoxide-based strategies for the synthesis of stereo-n-ads and application to polypropionate synthesis. A personal account

Cruz-Montañez

Morales-Rivera

Torres

et al. 2017

Inorganica Chimica Acta

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The enantioselective synthesis of polypropionates continues to be an attractive realm for the synthetic chemists mostly due to the challenges presented by the number of consecutive stereogenic centers contained within the aliphatic chain. Over the years, our laboratory has developed an epoxide-based three-step reiterative methodology for the construction of these targets, with the ultimate goal that the approach could be extended to the synthesis of polypropionate-containing natural products. The key steps include the diastereoselective epoxidation of allylic and homoallylic alcohols, and the regioselective cleavage of 2-methyl-3,4-epoxy alcohols. The choice of the organometallic reagent, and the cis/trans geometry of the chiral epoxide can be used to control both the relative and absolute configuration of the resulting propionate unit, allowing our approach to be applied in the synthesis of advanced fragments. Additionally, the combination of our first- and second-generation methodologies permits the incorporation of different variations at the methyl moiety.

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Total Synthesis of Mycalolides A and B through Olefin Metathesis

Cited by 32 publications

References 58 publications

Marine natural products

Marine natural products

Synthesis and Biological Activities of Aplyronine A Analogues toward the Development of Antitumor Protein–Protein Interaction Inducers between Actin and Tubulin: Conjugation of the C1–C9 Macrolactone Part and the C24–C34 Side Chain

Reiterative epoxide-based strategies for the synthesis of stereo-n-ads and application to polypropionate synthesis. A personal account

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