Diels-Alder reaction of 3-and 2-nitroindoles with Danishefsky's diene gives the expected 2-and 3-hydroxycarbazoles in very good to excellent yields (73-91%) and with apparent complete regioselectivity.
✦ LIBER ✦
Diels-Alder reactions of N-tosyl-3-nitroindole and dienamides: synthesis of intermediates ofAspidospermine alkaloids
✍ Scribed by Betina Biolatto; Mari´a Kneeteman; Pedro Mancini
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 228 KB
- Volume
- 40
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
N-tosyl-3-nitroindole undergoes high yielding Diels-Alder reactions with 1-(N-acyl-Nalkylamino)-l,3-butadienes in a regioselective manner, to afford advanced intermediates for the synthesis of Aspidospermine alkaloids.
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