The chemistry of thiocyanic esters

Erian, A. W.; Sherif, Sherif M.

doi:10.1016/s0040-4020(99)00386-5

Cited by 201 publications

(61 citation statements)

References 295 publications

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“…[34] This reaction sequence, as performed by Kibayashi and Funk, produces 1 in a small amount (~20 %) as the minor component in a mixture of at least three compounds. An elimination product and the isothiocyanate corresponding to 1 are also produced during this reaction sequence.…”

Section: Cross-coupling Experimentsmentioning

confidence: 99%

An Asymmetric Formal Synthesis of Fasicularin

Fenster

Dake

2004

Chemistry A European J

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An asymmetric formal synthesis of fasicularin (1) is described. This natural product, isolated from the extracts of the marine invertebrate Nephteis fasicularis, has shown modest cytotoxicity towards Vero cells. Fasicularin is among only two members of the cylindricine family of natural products, along with lepadiformine (2), to possess a trans A-B ring junction. Key steps of this approach to 1 involve a siloxy-epoxide semipinacol rearrangement of 5 to 6, a B-alkyl Suzuki-Miyaura coupling reaction by using enol trifluoromethanesulfonate 19 and a substrate-directed hydrogenation reaction of 24. This formal synthesis also highlights the difficulty in the incorporation of the thiocyanate functionality present in 1.

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Section: Cross-coupling Experimentsmentioning

confidence: 99%

An Asymmetric Formal Synthesis of Fasicularin

Fenster

Dake

2004

Chemistry A European J

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“…[14] Thanks to the good leaving group ability of the cyanide moiety their reactions with nucleophiles afford thioethers and thiophosphorus compounds. They are also highly susceptible to hydrolysis and reduction to form the corresponding thiols.…”

Section: Synthesis Of Thiolupanesmentioning

confidence: 99%

Synthesis and Cytotoxicity of 28a‐Homothiolupanes and 28a‐Homothiolupane Saponins

et al. 2015

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A concise synthesis of 28a-homo-28a-thiolupane triterpenes and the corresponding saponins containing D-mannose, D-idose, L-arabinose and L-rhamnose moieties was elaborated. New triterpenes were obtained from readily available 3-O-allylbetulinal by elongation of the carbon chain by Wittig reaction, followed by hydrolysis of the enol ether, reduction of the elongated aldehyde and nucleophilic substitution of the corresponding mesylate with thiocyanate ion. Saponins were obtained by glycosylation of triterpenes with classical Schmidt

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“…N,N-Dibenzyl-S-cyanothiohydroxylamine (7). ; ir: ν 3152, 3131, 3061, 3019, 2965, 2834, 2707, 2630, 2574, 2079, 1623, 1612, 1519, 1462, 1434, 1362, 1268, 1239, 1158, 1143, 1125, 1028, 874, 800 Compound 11 was prepared by the reaction of 3 with N-benzylaniline using Method A (reflux 4.5 h) in 59% (283 mg), mp 41-2 °C (cyclohexane); for 11, mp 78 °C (ethanol) is reported [22].…”

Section: N-benzyl-s-cyanothiohydroxylamine (6)mentioning

confidence: 99%

“…Thiocyanates play an important role in various fields of organosulfur chemistry [4], the thiocyanato group appears in a number of biologically active natural products [5], and thiocyanates are also important starting compounds for synthesizing heterocyclic compounds [6,7]. Study of their r e a c t i v i t y, therefore, is always relevant.…”

mentioning

confidence: 99%

1‐Methyl‐3‐phenyl‐3‐thiocyanato‐1H,3H‐quinoline‐2,4‐dione: A novel thiocyanating agent

Klásek

Mrkvička

2003

Journal of Heterocyclic Chem

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Under mild reaction conditions, the thiocyanato group is selectively transferred from 1‐methyl‐3‐phenyl‐3‐thiocyanato‐1H,3H‐quinoline‐2,4‐dione (3) to some nucleophiles. Aliphatic primary and secondary amines are converted to S‐cyanothiohydroxylamines, anilines afford p‐thiocyanatoanilines, Wittig reagent is thiocyanated in α‐position, and thiols are oxidized to disulfides.

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The chemistry of thiocyanic esters

Cited by 201 publications

References 295 publications

An Asymmetric Formal Synthesis of Fasicularin

An Asymmetric Formal Synthesis of Fasicularin

Synthesis and Cytotoxicity of 28a‐Homothiolupanes and 28a‐Homothiolupane Saponins

1‐Methyl‐3‐phenyl‐3‐thiocyanato‐1H,3H‐quinoline‐2,4‐dione: A novel thiocyanating agent

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