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New pyrano[3,4-b]indoles from 2-hydroxymethylindole and l-dehydroascorbic acid |
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| Authors: | Sergey N. Lavrenov Alexander M. Korolev Maria N. Preobrazhenskaya |
| Affiliation: | a Gause Institute of New Antibiotics, Russian Academy of Medical Sciences, B. Pirogovskaya 11, 119021 Moscow, Russia b Center for Drug Research, Russian Research Chimico-Pharmaceutical Institute, Zubovskaya 7, 119815 Moscow, Russia |
| Abstract: | 2-Hydroxymethylindole reacts with l-dehydroascorbic acid under mild conditions to give (3R,3aR,10cS)-3-[(1S)-1,2-dihydroxyethyl]-3a,10c-dihydroxy-3a,5,6,10c-tetrahydrofuro[3′,4′:5,6]pyrano[3,4-b]indol-1(3H)-one. Its tosyl derivative undergoes cyclization to form a pentacyclic ketal derivative. |
| Keywords: | l-Ascorbic acid l-Dehydroascorbic acid Ascorbigen Indolopyrane 2-Hydroxymethylindole |
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