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Diastereospecific synthesis of ketooxindoles. Potential intermediates for the synthesis of alstonisine as well as for Voachalotine related oxindole alkaloids

✍ Scribed by Peng Yu; James M Cook

Book ID: 104258409
Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 187 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)10420-8

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✦ Synopsis

A convenient method has been developed to convert Na-H tetracyclicketone la into the two corresponding oxindoles[C(7)l diastereospecifically. Treatment of the Na-H, Nb-benzyl tetracyclicketone la with t-BuOCl provided diastereomer 2a (related to Voacanga oxindoles), whereas the same process with Nb-H ( lb ) or Nb-benzoyl ( le ) substituted analogs funished the diastereomers 2b and 2c (related to alstonisine), respectively.

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