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Regioselective [2,3] sigmatropic rearrangement to the pyrrolo[3,2-e] indole ring system of CC-1065

โœ Scribed by Martha A Warpehoski; V.Susan Bradford

Book ID
104218712
Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
261 KB
Volume
27
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

A short and efficient synthesis of the 1,2-dihydro-3H-pyrrolo[3,2-elindole (2) ring system of the antitumor antibiotic CC-1065 (1) from ethyl-5-aminoindole-2-carboxylate 3 was made possible by the inherent regioselectivity of the [2,3] sigmatropic rearrangement of the azasulfonium ylide 4 and a thiation-reduction sequence for oxindole to indoline conversion. As part of our ongoing study of structure-activity relationships of analogs of the novel and highly potent antitumor antibiotic, CC-1065 (l)', we were interested in efficiently preparing the 1,2dihydro-3H-pyrrolo[3,2-elindole ring system (2) contained in the middle and right-hand segmentsof the natural product.2

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ChemInform Abstract: One-Step Syntheses
ChemInform Abstract: One-Step Syntheses of the Pyrrolo[3,4-b]indole and Pyrrolo[2,3-b]indole Ring Systems from 3-Nitroindoles.
โœ E. T. PELKEY; G. W. GRIBBLE ๐Ÿ“‚ Article ๐Ÿ“… 2010 ๐Ÿ› John Wiley and Sons โš– 32 KB ๐Ÿ‘ 1 views

One-Step Syntheses of the Pyrrolo[3,4-b]indole and Pyrrolo[2,3b]indole Ring Systems from 3-Nitroindoles. -3-Nitroindoles like (I) are converted into the corresponding protected derivatives (III). The compounds (III) react with isocyanides (IV) and (VI) under the Barton-Zard pyrrole synthesis conditi