A general synthesis of the acarnidines

Blunt, John W.; Munro, Murray H. G.; Yorke, Selwyn C.

doi:10.1016/s0040-4039(00)87460-2

Cited by 14 publications

(2 citation statements)

References 32 publications

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“…The tetrahydrofuran derivatives (5 1)- (54) and the diol (55) were obtained from ethanol extracts of Chondrosia ~o l l e c t r i x . ~~ A dichloromethane extract of the lyophilized sponge contained a 1 : 1 mixture of two epimeric acids ( 56) and (57), a 1 : 1 mixture of the corresponding methyl esters (58) and (59), and the hemiketal (52).29 Specimens of Plakortis zygompha that were collected at Belize could easily be (53) (54) distinguished by the characteristic sweet odour of 7-methyloct-4-en-3-one (60).49 Plakortis zygompha also contained the hydroxy-ketone (61), two esters (62) and (63), and a mixture of compounds from which (64) and (65) were isolated after acetylation. It is not clear whether these metabolites are of polyketide or terpenoid biosynthetic origin, or whether they are produced by the sponge or an epibiont.…”

Section: Spongesmentioning

confidence: 99%

Marine natural products: metabolites of marine invertebrates

Faulkner¹

1984

Nat. Prod. Rep.

327

154

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Section: Spongesmentioning

confidence: 99%

Marine natural products: metabolites of marine invertebrates

Faulkner¹

1984

Nat. Prod. Rep.

327

154

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“…The structure of NSTX-3, proposed as 2,4-dihydroxyphenylacetyl-asparaginyl-(arginyl-cadaverino--alanyl)-cadaverine (639), was established by spectroscopic analysis (787,788). (642) TOKI et al (792) have isolated and identified compounds from N ephila clavata named nephilatoxins-7 (643), -8 (644) and -9 (645). (639) (640) From Argiope aurantia, ADAMS et al (791) isolated the argiotoxins AR659 (641) and AR673 (642), in which the 2,4-dihydroxyphenylacetyl acid residue is replaced by a 4-hydroxyindole-3-acetyl group.…”

Section: Spidersmentioning

confidence: 99%

Some Aspects of Guanidine Secondary Metabolites

Berlinck

1995

Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

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Oxidation of Alcohols to Carbonyl Compounds via Alkoxysulfonium Ylides: TheMoffatt,Swern, and Related Oxidations

Tidwell

1990

Organic Reactions

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The use of dimethyl sulfoxide as an oxidizing agent began with the discoveries by Kornblum and co‐workers that certain α‐bromo ketones were converted into glyoxals under mild conditions by treatment with dimethyl sulfoxide, and that primary tosylates such as n ‐octyl tosylate were converted into the corresponding aldehydes using dimethyl sulfoxide and sodium bicarbonate at 150° for 3 minutes. The initial step of the reactions involves a displacement by dimethyl sulfoxide giving an alkoxysulfonium ion and this species undergoes a 1,2 elimination assisted by base to give the carbonyl product A few years later it was discovered that alcohols were oxidized at room temperature to carbonyl compounds by dimethyl sulfoxide, dicyclohexylcarbodiimide (DCC), and phosphoric acid. This reaction was immediately recognized as an effective and mild procedure for sensitive substrates, and the extensive studies by this group and the development of alternative variations elsewhere have been the subject of several earlier reviews. The course of the Moffatt procedure is summarized. The key intermediate in this process is the oxysulfonium ylide, which appears to be common to all of the variations of dimethyl sulfoxide oxidations, and which reacts intramolecularly to give the products. Other related procedures that were soon developed utilize dimethyl sulfoxide activated by acetic anhydride, phosphorus pentoxide, sulfur trioxide/pyridine complex, and chlorine. Reaction of alcohols with phosgene to give chloroformates which react with dimethyl sulfoxide to give alkoxysulfonium ions, followed by reaction with triethylamine, also effects oxidation. The reaction of the complexes of dimethyl sulfide and chlorine or N ‐chlorosuccinimide (NCS) with alcohols is proposed to give the same alkoxysulfonium complexes, which are efficiently converted into carbonyl products upon addition of triethylamine. Electrochemical activation of sulfides has also been successfully utilized. The activation of dimethyl sulfoxide is effected by many reagents, and these reactions as well as those involving activated sulfides evidently involve the alkoxysulfonium ion and the decisive oxidation step which occurs via the alkoxysulfonium ylide in all the reactions. Activation of dimethyl sulfoxide by oxalyl chloride, has become the most used of these oxidation procedures, but several of the other methods are also convenient and efficient.

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A general synthesis of the acarnidines

Cited by 14 publications

References 32 publications

Marine natural products: metabolites of marine invertebrates

Marine natural products: metabolites of marine invertebrates

Some Aspects of Guanidine Secondary Metabolites

Oxidation of Alcohols to Carbonyl Compounds via Alkoxysulfonium Ylides: TheMoffatt,Swern, and Related Oxidations

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