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A Unified Route to theWelwitindolinone Alkaloids: Total Syntheses of ( − )- N -MethylwelwitindolinoneC Isothiocyanate, ( − )- N -MethylwelwitindolinoneC Isonitrile, and ( − )-3-Hydroxy- N -methylwelwitindolinoneC Isothiocyanate

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ABSTRACT

2a2b3a2a2b3a3a: As part of a comprehensive strategy to the welwitindolinonealkaloidspossessing a bicyclo[4.3.1]decane core, we report herein concise asymmetrictotal syntheses of (−)-N-methylwelwitindolinoneC isothiocyanate (), (−)-N-methylwelwitindolinoneC isonitrile (), and (−)-3-hydroxy-N-methylwelwitindolinone C isothiocyanate () from acommon tetracyclic intermediate. The crucial vinyl chloride moietywas installed through electrophilic chlorination of a hydrazone, butonly after adjustment of reactivity to circumvent a facile skeletalrearrangement. Selective desulfurization and oxidation of provided access to and , respectively.Notably, this work provides corrected 1H and 13C NMR spectral data for .

No MeSH data available.


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A Unified Route to theWelwitindolinone Alkaloids: Total Syntheses of ( − )- N -MethylwelwitindolinoneC Isothiocyanate, ( − )- N -MethylwelwitindolinoneC Isonitrile, and ( − )-3-Hydroxy- N -methylwelwitindolinoneC Isothiocyanate
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3368435&req=5

View Article: PubMed Central - PubMed

ABSTRACT

2a2b3a2a2b3a3a: As part of a comprehensive strategy to the welwitindolinonealkaloidspossessing a bicyclo[4.3.1]decane core, we report herein concise asymmetrictotal syntheses of (−)-N-methylwelwitindolinoneC isothiocyanate (), (−)-N-methylwelwitindolinoneC isonitrile (), and (−)-3-hydroxy-N-methylwelwitindolinone C isothiocyanate () from acommon tetracyclic intermediate. The crucial vinyl chloride moietywas installed through electrophilic chlorination of a hydrazone, butonly after adjustment of reactivity to circumvent a facile skeletalrearrangement. Selective desulfurization and oxidation of provided access to and , respectively.Notably, this work provides corrected 1H and 13C NMR spectral data for .

No MeSH data available.