Total synthesis of (29S,37S)-isomer of malevamide E, a potent ion-channel inhibitor

Gajula, Praveen Kumar; Sharma, Sheena; Ampapathi, Ravi Sankar; Chakraborty, Tushar Kanti

doi:10.1039/c2ob26533h

Cited by 5 publications

(3 citation statements)

References 36 publications

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“…452 Convergent synthesis of (29S,37S)-malevamide E involving Julia-Kocienski olenation, Urpi acetal aldol and Shiina macrolactonisation reactions has been achieved but a mismatch of the NMR data between the synthetic and natural samples indicated that the originally assigned congurations of some of the amino acids need revision. 453 A stereoselective synthesis of the C-43-C-67 fragment of amphidinol 3, originally obtained from the dinoagellate Amphidinium klebsii, 454 revised the originally assigned conguration at C-51 from (R) to (S). 455 Ieodomycins A and B are antimicrobial fatty acids originally obtained from a Bacillus sp.…”

Section: Synthetic Aspectsmentioning

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: Synthetic Aspectsmentioning

confidence: 99%

Marine natural products

et al. 2015

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“…We have observed broadness of the resonances for 12 due to the rotation of the N -Me group of Ala. This is a common phenomenon observed among N -methylated peptides . However, for both 11 and 12 , the coupling constant values and NOEs for the pyrrolidine ring were similar, as observed in 10b .…”

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confidence: 99%

“…This is a common phenomenon observed among N-methylated peptides. 16 However, for both 11 and 12, the coupling constant values and NOEs for the pyrrolidine ring were similar, as observed in 10b. These observations suggested that the pyrrolidine ring in these peptides is also in Cγ-exo conformation.…”

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confidence: 99%

Diastereoselective Synthesis of 5-Heteroaryl-Substituted Prolines Useful for Controlling Peptide-Bond Geometry

Ali¹,

Singh

Singh³

et al. 2016

Org. Lett.

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A versatile diastereoselective Friedel-Crafts alkylation reaction of heteroaryl systems with a cyclic enecarbamate for the preparation of 5-heteroaryl-substituted proline analogues in good yields has been developed. These heterocyclic tethered cyclic amino acid building blocks constitute important structural motifs in many biologically active molecules. The impact of the substitution on proline cis/trans isomerization was explored by carrying out solution conformational studies by NMR on 5-furanyl-substituted proline-containing peptides. Conformational analysis revealed that the peptide bond is constrained in an exclusively trans conformation.

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TheJulia–Kocienski Olefination

Blakemore¹,

Sephton

Ciganek

2018

Organic Reactions

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The Julia–Kocienski olefination is a direct connective synthesis of alkenes via the addition of metalated aryl alkyl sulfones to carbonyl compounds. The activating aromatic group associated with the sulfone must possess electrophilic character, and alkene formation occurs via β‐alkoxy sulfone formation, transfer of the aryl group from sulfur to oxygen via a Smiles rearrangement, and then elimination of sulfur dioxide and an aryloxide anion from the resulting β‐aryloxy sulfinate anion. The olefination process itself and the methods used to prepare the requisite sulfone substrates are tolerant of a wide variety of functional groups, and a variety of alkene targets can be prepared. Stereoselectivity is dependent on the nature of the sulfone, the carbonyl compound, the activating aryl moiety, and the reaction conditions. This chapter describes theoretical and operational aspects of the Julia–Kocienski olefination such that the reader will be able to obtain optimal results in his/her own research. A detailed mechanistic overview is included to account for the factors that influence stereoselectivity and yield. Methods for introducing sulfone activators into fragments of interest, best practices for generating sulfone anions, and optimal strategies for targeting different classes of alkene targets are discussed. Functional group compatibilities, reaction variants, and a comparison to other methods of alkene synthesis are also presented. Tabular surveys are organized according to type of alkene synthesized, with an emphasis on the degree of substitution and the level of conjugation about the newly formed double bond. The literature is covered from the initial disclosure of the Julia–Kocienski olefination in 1991 to the first quarter of 2016.

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Total synthesis of (29S,37S)-isomer of malevamide E, a potent ion-channel inhibitor

Cited by 5 publications

References 36 publications

Marine natural products

Marine natural products

Diastereoselective Synthesis of 5-Heteroaryl-Substituted Prolines Useful for Controlling Peptide-Bond Geometry

TheJulia–Kocienski Olefination

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