Diterpenoid isocyanides from the marine sponge hymeniacidon amphilecta

Wratten, Stephen J.; Faulkner, D. John; Hirotsu, Ken; Clardy, Jon

doi:10.1016/s0040-4039(01)95220-7

Cited by 64 publications

(59 citation statements)

References 4 publications

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“…The combined organic extracts were washed with brine, dried (MgSO,), and concentrated. Drip column chromatography of the residual oil on silica gel (10 g, 1 To a stirred solution of the diene 7 (190 mg, 0.542 mmol) in dry diethyl ether (5 mL) was added neat NE (9) (0.6 mL). After the mixture had been stirred at room temperature for 3 h, the solvent was removed under reduced pressure.…”

Section: Prepnrntiotz Of the Enone Ester 35mentioning

confidence: 99%

“…The structurally novel marine natural product (-)-8,15-diisocyano-1 1 (20)-amphilectene, obtained from the sponge Hymeniacidon amphilecta, has been shown by X-ray diffraction analysis to possess the constitution and relative stereochemistry depicted in structural formula 1 (1). This substance is a member of the small family of biologically active amphilectane-type diterpenoids that share the carbon skeleton 2 (1)(2)(3).…”

Section: Introductionmentioning

confidence: 99%

“…This substance is a member of the small family of biologically active amphilectane-type diterpenoids that share the carbon skeleton 2 (1)(2)(3).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of functionalized hexahydro-, octahydro-, and decahydro-1H-phenalenes via Diels–Alder reactions of 1-methylene-4a-methoxycarbonyl-1,2,3,4,4a,5,6,7-octahydronaphthalene and related dienes

Piers¹,

Friesen²,

Kao³

et al. 1993

Can. J. Chem.

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The results of a study of Diels–Alder reactions of the bicyclic dienes 6–8 with a variety of dienophiles are reported. Although 6 and 7 undergo cycloaddition reactions smoothly and efficiently, thermal Diels–Alder reactions of 8 are generally sluggish or, under the conditions investigated, do not proceed at all. Additions of tetracyanoethylene (TCNE) to 6–8 are highly face-selective, with preferential attack of the dienophile on the side of the dienes opposite to the angular methoxycarbonyl group. Reaction of 7 with maleic anhydride (MAN) is completely face-selective and proceeds preferentially via an endo transition state. Diels–Alder reactions of 6 and 7 with methyl acrylate (MAC) and nitroethylene (NE) are entirely regioselective, but the face-selectivities, which vary from ~2:1 to ~3:1, are rather low. The use of this chemistry as a method for the synthesis of functionalized, stereochemically defined, perhydro-1H-phenalenes is demonstrated.

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Section: Prepnrntiotz Of the Enone Ester 35mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of functionalized hexahydro-, octahydro-, and decahydro-1H-phenalenes via Diels–Alder reactions of 1-methylene-4a-methoxycarbonyl-1,2,3,4,4a,5,6,7-octahydronaphthalene and related dienes

Piers¹,

Friesen²,

Kao³

et al. 1993

Can. J. Chem.

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“…Amphilectane and cycloamphilectane are trivial names proposed [60,61] for the compounds derived from two sponges, an Amphimedon sp. from Australia and Hymeniacidon amphilecta (order: Halichondrida) from the Caribbean.…”

Section: Amphilectane-cycloamphilectanementioning

confidence: 99%

“…Two related tricyclic diterpenes, diisocyano 96 and isocyanoformamido 97, were discovered as a result of antibacterial monitoring during workup of H. amphilecta [60]. Both compounds upon hydrolysis yielded the expected diformamide.…”

Section: Amphilectane-cycloamphilectanementioning

confidence: 99%

Marine isocyano compounds

Chang

Scheuer

Topics in Current Chemistry

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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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Diterpenoid isocyanides from the marine sponge hymeniacidon amphilecta

Cited by 64 publications

References 4 publications

Synthesis of functionalized hexahydro-, octahydro-, and decahydro-1H-phenalenes via Diels–Alder reactions of 1-methylene-4a-methoxycarbonyl-1,2,3,4,4a,5,6,7-octahydronaphthalene and related dienes

Synthesis of functionalized hexahydro-, octahydro-, and decahydro-1H-phenalenes via Diels–Alder reactions of 1-methylene-4a-methoxycarbonyl-1,2,3,4,4a,5,6,7-octahydronaphthalene and related dienes

Marine isocyano compounds

Porifera (Sponges)–2

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