Total Synthesis of (−)-Bitungolide F and Determination of Its Absolute Stereochemistry

Ghosh, Subhash; Kumar, S. Uday; Shashidhar, J.

doi:10.1021/jo7023152

Cited by 31 publications

(9 citation statements)

References 21 publications

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“…23 Submitting phosphonate 3a and commercially available (−)-Corey-aldehyde/lactone 4 to the Masamune-Roush modification of the Horner-Wadsworth-Emmons reaction yielded the key enone 5a in 92% yield. 24 Under the experimental conditions used this reaction gave the E geometrical isomer exclusively, as confirmed by 1 H NMR data ( 3 J CH=CH = 15.8 Hz). Reduction of compound 5a followed two different paths (Scheme 2).…”

supporting

confidence: 55%

Novel tail and head group prostamide probes

Finnegan

Shelnut

Nikas

et al. 2015

Bioorganic & Medicinal Chemistry Letters

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We report the design and synthesis of novel prostaglandin-ethanolamide (PGE2-EA) analogs containing head and tail group modifications to aid in the characterization of a putative prostamide receptor(s). Our synthetic approach utilizes Horner-Wadsworth-Emmons and Wittig reactions to construct the head and the tail moieties of the key PGE2 precursor, which leads to the final products through a peptide coupling, Swern oxidation and HF/pyridine assisted desilylation. The synthesized analogs were shown not to interact significantly with endocannabinoid proteins and recombinant EP1, EP3 and EP4 receptors and suggest a yet to be identified prostamide receptor as their site(s) of action.

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supporting

confidence: 55%

Novel tail and head group prostamide probes

Finnegan

Shelnut

Nikas

et al. 2015

Bioorganic & Medicinal Chemistry Letters

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“…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. 347 A two-sponge association of Poecillastra wondoensis and a Jaspis species (Keomun Is., South Korea) contained the styrene derivatives 332-336, 348 while a naphthahydroquinone derivative, xestosaprol C 337, was isolated from Xestospongia sapra (Kerama Islands, Okinawa).…”

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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“…According to Ghosh et al., adding (Z)‐enolate of 38.1 to the aldehyde 39.1 in the presence of TiCl 4 and (−)‐sparteine at 0 °C using Crimmins’ protocol garnered an aldol adduct 39.2 with excellent diastereoselectivity (98 : 2 dr) (Scheme 39). [49] …”

Section: Oxazolidinone Chiral Auxiliaries‐induced Asymmetric Synthesismentioning

confidence: 99%

TiCl₄‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

2021

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Nature is incessantly affianced to construct bioactive and structurally intriguing compounds with magnificent three‐dimensional frameworks in the Universe. The inadequacy of these naturally occurring precious compounds prompted several minds of chemists to synthesise them in a laboratory for a thorough evaluation of their medicinal and clinical properties via a structure‐activity relationship study. Finding an optimised methodology to synthesise chiral natural products has always been challenging in synthetic organic chemistry, particularly the formation of asymmetric carbon‐carbon bonds adhering to the existing stereochemistry. In this context, chiral auxiliaries have proven to be effective tools for inducing chirality during the synthesis of chiral molecules. In fact, the chiral auxiliary will allow us to control the synthesis of many enantiomerically pure isomers in natural product synthesis. In this area, the significant contribution of the Evans’ chiral auxiliary in TiCl4‐mediated asymmetric aldol reactions to the installation of known configurations in organic synthetic chemistry motivated us to compile an exhaustive and systematic summary of the relevant research findings published in the last two decades.

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Total Synthesis of (−)-Bitungolide F and Determination of Its Absolute Stereochemistry

Cited by 31 publications

References 21 publications

Novel tail and head group prostamide probes

Novel tail and head group prostamide probes

Marine natural products

TiCl₄‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

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Total Synthesis of (−)-Bitungolide F and Determination of Its Absolute Stereochemistry

Cited by 31 publications

References 21 publications

Novel tail and head group prostamide probes

Novel tail and head group prostamide probes

Marine natural products

TiCl4‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

Contact Info

Product

Resources

About

TiCl₄‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis