Latrunculins: NMR study, two new toxins and a synthetic approach

Kashman, Yoel; Groweiss, Amiram; Lidor, R.; Blasberger, D.; Carmely, S.

doi:10.1016/s0040-4020(01)96553-6

Cited by 59 publications

(48 citation statements)

References 5 publications

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“…Table 2. A COSY experiment showed the following correlations: 2-4',19; 4'-4, 5',5;[4][5]5;5',[5][6]7;[6][7][7][8][8][9]20;10',10;[9][10]10;10,[11][12]12;13',13;13;14;[13][14]14;17,NH. Tables 1 and 3. (2) = 9.7, 4.9, 18-H), 3.69 (m, 13-, 15-H), 3.42 (dd, J = 11.8, 9.7, 19-H'), 3.34 (s,OCH,),3.25 (m,.…”

Section: Isolation Of 67-epoxy-latmentioning

confidence: 99%

“…(2) = 9.7, 4.9, 18-H), 3.69 (m, 13-, 15-H), 3.42 (dd, J = 11.8, 9.7, 19-H'), 3.34 (s,OCH,),3.25 (m,. (3) 4.97dd (11,9) 4.15111…”

Section: Isolation Of 67-epoxy-latmentioning

confidence: 99%

“…3.75dd (9,6) 3.40dd (12,9) 3.32dd (12,6) 2.58td (12,6) (9,6) 3.24111 3.49dd (12,9) 3.24111 3.41dd (12,6) 3.32m…”

Section: -Methoxy-latmentioning

confidence: 99%

“…[MH+ -COJ, 464 (1) (d,J = 6.1,, 0.68 (d,J = 6.1,). A COSY experiment (C6D6) showed the following correlations: 2-4',21; 4'-4, 5',5,6;[4][5]5;5',[5][6]7,9;[6][7]8,9;[7][8]9;[8][9][9][10]11,22;I2',12;[11][12]12;13;[12][13]15,16;[14][15][15][16]16;19',19;19; 17-OCH-CH;,CH3; 15-OCH-CH;,CH3. (C,D,) showed the following correlations: 2-21; 4'-4, 5',5; 4-5',5; 5',5-6,7; 6-(ddd, J = 9.6, 3.2, 1.6, 18-H), 3.53 (bs, 15-H), 3.32 (td, J = 11.8, 7; 7-8,9; 8-9; 9.10; 10-11 ',22;12',i2;[11][12]12;13;…”

Section: 88mmentioning

confidence: 99%

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On the Chemistry of Latrunculins A and B

et al. 1989

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Section: Isolation Of 67-epoxy-latmentioning

confidence: 99%

“…(2) = 9.7, 4.9, 18-H), 3.69 (m, 13-, 15-H), 3.42 (dd, J = 11.8, 9.7, 19-H'), 3.34 (s,OCH,),3.25 (m,. (3) 4.97dd (11,9) 4.15111…”

Section: Isolation Of 67-epoxy-latmentioning

confidence: 99%

“…3.75dd (9,6) 3.40dd (12,9) 3.32dd (12,6) 2.58td (12,6) (9,6) 3.24111 3.49dd (12,9) 3.24111 3.41dd (12,6) 3.32m…”

Section: -Methoxy-latmentioning

confidence: 99%

Section: 88mmentioning

confidence: 99%

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On the Chemistry of Latrunculins A and B

et al. 1989

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“…The absolute configuration of latrunculin-A was determined by X-ray analysis, and chemical degradation. 91 In the same year, Swinholide-A (266), a 22-membered macrolide, was isolated from the Red Sea sponge Theonella swinhoei. 92 Six brominated unsaturated polyenynic C9-, C16-, and C18-acids (267-272) were isolated from the marine sponge Xestospongia, collected from the Gulf of Eilat, Red Sea.…”

Section: Other Metabolitesmentioning

confidence: 99%

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2017

IJPSR

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Porifera (Sponges)–2

Kornprobst

2014

Encyclopedia of Marine Natural Products

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The article contains sections titled: Secondary Metabolites of Hadromerida and Chondrosida Perforating Power of Clionaidae lyso ‐Phospholipids and Sulfated Sphingosines of Spirastrella abata Brominated Acetylenic Derivatives of Diplastrella Cyclic Peroxides Terpenes Unconventional Sterols Macrolactones: Latrunculins and Spongistatins Atypical Glycosides of Latrunculia corticata Other Nitrogen‐Free Toxins Peptides and Depsipeptides Pyrrole Derivatives and other Nitrogen‐Containing Heterocycles Atypical Nucleosides Secondary Metabolites of Lithistida Particular Characteristics of Lithistid Sponges Unusual Halogenated Fatty Acids Nitrogen‐Containing Sesquiterpenes of Theonella Specific Glycolipids of Theonella swinhoei, Discodermia calyx and D. dissoluta Long‐Chain Polyacetylenic Derivatives of Theonella sp 3β‐Methoxysterols of Jereicopsis graphidiophora 4‐Methylene Sterols and Sterones of Theonella Macrolides Examples of Acetogenins: Discodermolide, Calyculins, and Onnamides Linear Amides and Peptides Mono‐ and Bicyclic Peptides Symbiotic Origin of Some Polypeptides Cyclic and Linear Depsipeptides Atypical Nitrogenous Derivatives Secondary Metabolites of Spirophorida Atypical Sterols of Cinachyra, Microscleroderma , and Scleritoderma Cinachyrolide A, Enigmazole A Microsclerodermins and Aciculitins Examples of Atypical Derivatives of Some Sponges of the Tetillidae Secondary Metabolites of Agelasida Sterols Diterpenes and Carotenoids Gracilioethers of Agelas gracilis Merosesquiterpenes and Nitrogen‐Containing Meroditerpenes Galactosylceramides and Glycolipids Oroidin and Related C 11 N 5 Bromopyrrole Alkaloids Oroidin Series Agelastatin A Series Other Series Pyrrole‐2‐carboxylic Acid Derivatives Other Examples of Nitrogen‐Containing Heterocycles Betaines Secondary Metabolites of Halichondrida A‐ nor ‐Steroids and Other Nonconventional Sterols Conventional Terpenes Nitrogen‐Containing Terpenes: Isonitriles and Related Derivatives Other Terpenes Long‐Chain Linear Polyamines and α,ω‐bis‐isothiocyanates Polyethers: Halichondrins, Okadaic, and Glycookadaic Acids Various Lipids Linear Peptides of the Genera Auletta and Cymbastela Depsipeptides and Cyclic Peptides Unusual Amino Acids and Betaines Pyrrole, Imidazole, Pyridine, Isoquinoline, and Indole Derivatives Pyrrole Derivatives Imidazole Derivatives Pyridine and Isoquinoline Derivatives Indole Derivatives Heterocycles Related to the Oroidin Family Atypical Halogenated and Sulfur‐Containing Derivatives

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Latrunculins: NMR study, two new toxins and a synthetic approach

Cited by 59 publications

References 5 publications

On the Chemistry of Latrunculins A and B

On the Chemistry of Latrunculins A and B

Untitled

Porifera (Sponges)–2

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