Haliclonacyclamines A and B, cytotoxic alkaloids from the tropical marine sponge Haliclona sp

Charan, Romila D.; Garson, Mary J.; Brereton, Ian M.; Willis, Anthony C.; Hooper, John N. A.

doi:10.1016/0040-4020(96)00436-x

Cited by 82 publications

(52 citation statements)

References 27 publications

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“…A combination of HSQC, HMBC, DQFCOSY, and HOHAHA experiments led to an initial structural assignment of haliclonacyclamine B. 35 The assigned structure was supported by In 1998 Garson and co-workers published a correction of the original haliclonacyclamine B (3.4) structural assignments. 36 The minor correction relocated the cis carbon-carbon double bond from the C30-C29 to C28-C27 position.…”

Section: Haliclonacyclaminesmentioning

confidence: 99%

“…Despite the challenges encountered during structure elucidation of tetracyclic 3-alkylpiperidines, Crews, Garson, Berlinck, Kashman, and co-workers have isolated and determined structure for over sixteen tetracyclic alkaloids. [33][34][35][36][37]105,106 This chapter will examine structural differences and the assignment of relatively stereochemistry among this subgroup of 3-alkylpiperidine alkaloids.…”

Section: Introductionmentioning

confidence: 99%

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Total Synthesis of (±)‐Haliclonacyclamine C

Smith

Sulikowski

2010

Angew Chem Int Ed

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Section: Haliclonacyclaminesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Total Synthesis of (±)‐Haliclonacyclamine C

Smith

Sulikowski

2010

Angew Chem Int Ed

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“…Impurities leading to Crews, Garson, Berlinck, Kashman, and co-workers have isolated and determined structure for over sixteen tetracyclic alkaloids. [33][34][35][36][37]105,106 This chapter will examine structural differences and the assignment of relatively stereochemistry among this subgroup of 3-alkylpiperidine alkaloids.…”

Section: Introductionmentioning

confidence: 99%

“…6 The structural variations within this sub-group primarily occur in the relative stereochemistry of the 3,4-linked bis-piperidine core and the degree and location of unsaturation in the two appending macrocycles. [33][34][35][36][37]105,106 Due to subtle variations in their complex framework, the structure elucidation of many tetracyclic alkaloids has been extremely challenging. Rigorous NMR studies using in depth experiments were required for structural assignment of this group of alkylpiperidines.…”

Section: Introductionmentioning

confidence: 99%

“…Another growing class of biologically active compounds derived from 3-alkylpyridines is the tetracyclic alkaloids, which features a 3,4-linked bis-piperidine core attached to two macrocycles. [33][34][35][36][37] In 1994 Crews and coworkers isolated halicyclamine A(1.68) 33 from the marine sponge Haliclona sp which has recently been evaluated as a lead for the discovery of new anti-tuberculosis agents. 38 The hypothetical biosynthesis of halicyclamine A (1.68) is outlined in Scheme 13.…”

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confidence: 99%

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Total Synthesis of (±)‐Haliclonacyclamine C

Smith

Sulikowski

2010

Angewandte Chemie

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Porifera (Sponges)–3

Kornprobst

2014

Encyclopedia of Marine Natural Products

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The article contains sections titled: Secondary Metabolites of Haplosclerida Acetylenic Derivatives 1‐Glyceryl Ethers from the Assemblage Ceratodictyon/Spongiosum/Haliclona/Cymaeformis Atypical Fatty Acids Terpenes and Meroterpenes Triterpenic Glycosides Hopanoids, Steroids and Sterosides Macrolides, Depsipeptides, and Cyclic Peptides Aminoalcohols and Glycosphingolipids (Cerebrosides) Manzamines and Related Derivatives Quinolizidine and 1‐Oxaquinolizidine Derivatives Pyridine Derivatives and 3‐alkylpyridinium Salts Pyridoacridine Alkaloids Pyrroloquinones and Other Examples of Nitrogen‐Containing Heterocycles Quinones and Sulfated Hydroquinones Very Long‐Chain Linear Sulfated Derivatives Thiocyanatins: α,ω‐Dithiocyanates of Oceanapia sp Some Information on Freshwater Haplosclerid Sponges Secondary Metabolites of Poecilosclerida Sterols, Steroids, and Sterosides Terpenes and Triterpenic Glycosides Polybrominated Acetogenins and Oxylipins Long‐Chain Acetylenic Derivatives: Raspailynes Glycolipids Brominated Aromatic Derivatives of Hamigera tarangaensis Macrolides Chondropsins: Cyclic Depsipeptides of Chondropsis sp Eurypamides ( Microciona eurypa ), Microcionamides ( Clathria abietina ) and Other Cyclic Peptides Linear Amides and Peptides Examples of Some Atypical Sulfur‐Containing Derivatives Pyrrole and Indole Derivatives Pyridines, Quinolizines, and Pyridoacridines Guanidine Derivatives Pyrroloiminoquinones and Pyrroloquinones Azasugars and Cyclic Amines Other Examples of Polycyclic Alkaloids Phosphorus‐ and Arsenic‐Containing Derivatives, Betaines

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Haliclonacyclamines A and B, cytotoxic alkaloids from the tropical marine sponge Haliclona sp

Cited by 82 publications

References 27 publications

Total Synthesis of (±)‐Haliclonacyclamine C

Total Synthesis of (±)‐Haliclonacyclamine C

Total Synthesis of (±)‐Haliclonacyclamine C

Porifera (Sponges)–3

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