Concise synthesis of (±)-horsfiline and (±)-coerulescine by tandem cyclisation of iodoaryl alkenyl azides
- 29 November 2002
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Organic & Biomolecular Chemistry
- Vol. 1 (1) , 117-122
- https://doi.org/10.1039/b208114h
Abstract
A brief, efficient and economical synthesis of the spiropyrrolidinyloxindoles, horsfiline and coerulescine, has been achieved, starting from itaconic acid and, respectively, p-anisidine or o-iodoaniline. Tandem radical cyclisation of iodoaryl alkenyl azides is the key step in both syntheses.Keywords
This publication has 32 references indexed in Scilit:
- A novel and economical route to (±)-horsfiline using an aryl iodoazide tandem radical cyclisation strategyChemical Communications, 2001
- Kurze Synthesen der SpirotryprostatineNachrichten aus der Chemie, 2000
- Preparation and a Novel Rearrangement Reaction of 1,2,3,4-Tetrahydro-9-hydroxy-b-carboline, and Their Applications for the Total Synthesis of (±)-CoerulescineHETEROCYCLES, 2000
- Total Synthesis of Spirotryprostatin A, Leading to the Discovery of Some Biologically Promising AnaloguesJournal of the American Chemical Society, 1999
- Total Synthesis of (−)-Horsfiline via Asymmetric NitroolefinationThe Journal of Organic Chemistry, 1999
- Oxindoles from Phalaris coerulescensPhytochemistry, 1998
- General and Facile Synthesis of Indoles with Oxygen-Bearing Substituents at the Benzene MoietyThe Journal of Organic Chemistry, 1997
- Synthesis of 1,3‐dihydro‐3,3‐dimethyl‐2H‐indol‐2‐one derivatives as possible nonsteroidal cardiotonicsJournal of Heterocyclic Chemistry, 1995
- On the Synthesis of the Oxindole Alkaloid: (±)-HorsfilineHETEROCYCLES, 1994
- Studies in biomimetic alkaloid syntheses. 2. Synthesis of vincadifformine from tetrahydro-.beta.-carboline through a secodine intermediateThe Journal of Organic Chemistry, 1978