Total Synthesis of Two Possible Diastereomers of (+)-Sarcophytonolide C and Its Structural Elucidation

Takamura, Hiroyoshi; Iwamoto, Kohei; Nakao, Eiji; Kadota, Isao

doi:10.1021/ol400157s

Cited by 15 publications

(8 citation statements)

References 36 publications

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“…807 synthesised via a route including macrolactonisation and transannular RCM steps has conrmed the structure and established the absolute conguration of the NP. 846 A general strategy for the synthesis of cladiellin diterpenoid NPs has been exemplied with the synthesis of ten examples. 847 Efforts to mimic the putative carbon-centred radical reactions proposed for the biosynthesis of selected norcembranoids in Sinularia sp.…”

Section: Sesquiterpenes Capillosananementioning

confidence: 99%

Marine natural products

et al. 2015

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This review covers the literature published in 2013 for marine natural products (MNPs), with 982 citations (644 for the period January to December 2013) 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 (1163 for 2013), 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: Sesquiterpenes Capillosananementioning

confidence: 99%

Marine natural products

et al. 2015

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“…Despite additional geometric issues in forming alkene macrocycles, especially to achieve cis-selectivity, RCM is an elegant way to access even the most challenging of natural product frameworks . Although relatively scarce in the assembly of complex cembranolides, relevant reports to our current study of bielschowskysin ( 1 ), a highly oxygenated tricyclo[9.3.0.0 2,10 ]tetradecane isolated from Pseudopterogorgia kallos, include the total synthesis of deoxypukalide and sarcophytonolide C. , …”

Section: Introductionmentioning

confidence: 99%

Cis Selective RCM Study to the 14-Membered Cyclic Subunit of Bielschowskysin

et al. 2021

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A concise, (Z)-selective ring-closing metathesis (RCM) route to the 14-membered carbocycle of bielschowskysin is detailed using naturally occurring chiral starting materials. Unproductive RCM substrates were attributed to alkyne chelation of the ruthenium catalyst and steric disadvantages within the cembranoid precursors, which was eventually circumvented by using cyclic diol benzylidene protection involving a C8-quaternary carbinol center.

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“…This type of secondary metabolites not only display a library of diverse intriguing structural features, but also exhibit a wide spectrum of biological activities, including cytoprotective, cytotoxic, anti-inflammatory, and other bioactive properties, 1,2 making them attractive targets for chemical synthesis. 3,4 The soft coral Sarcophyton trocheliophorum is a widespread member of the coral reef in the South China Sea. Recently, as part of our ongoing research project aimed at discovering bioactive substances from Chinese marine invertebrates, [5][6][7][8][9] we collected the title soft coral, off Yalong Bay, Hainan Province, China.…”

Section: Introductionmentioning

confidence: 99%

Structural, stereochemical, and bioactive studies of cembranoids from Chinese soft coral Sarcophyton trocheliophorum

et al. 2018

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A series of highly oxidative new cembranoids with diverse structural features such as a dienoate moiety (sarcophytonolides S -U, 1 -3) or an α,β-unsaturated ε-lactone (sartrolides H -J, 4 -6) were obtained from Hainan soft coral Sarcophyton trocheliophorum, along with known related analogues 7 -13. It is an extremely challenging work to determine the absolute configurations of these metabolites. For compounds 1, 3 and 4, solution TDDFT calculation of ECD and specific rotation were applied in combination with conformational analysis and NMR data to determine their relative and absolute configurations, leading to the revision of relative configuration of 14. The absolute configurations of compounds 8 -10 were determined by the solid-state TDDFT-ECD approach, and that of 8 was further confirmed by single-crystal X-ray diffraction experiment with Cu Kα radiation. In the bioassays, compound 8 exhibited not only moderate protein tyrosine phosphatase 1B (PTP1B) inhibitory activity (IC50 = 15.4 µM) but also moderate antibacterial activity against Staphylococcus aureus Newman strain (MIC50 = 250 µM).

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Total Synthesis of Two Possible Diastereomers of (+)-Sarcophytonolide C and Its Structural Elucidation

Cited by 15 publications

References 36 publications

Marine natural products

Marine natural products

Cis Selective RCM Study to the 14-Membered Cyclic Subunit of Bielschowskysin

Structural, stereochemical, and bioactive studies of cembranoids from Chinese soft coral Sarcophyton trocheliophorum

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