Concise synthesis of (±)-horsfiline and (±)-coerulescine by tandem cyclisation of iodoaryl alkenyl azides

D.E. Lizos; J.A. Murphy

doi:10.1039/b208114h

Concise synthesis of (±)-horsfiline and (±)-coerulescine by tandem cyclisation of iodoaryl alkenyl azides

D.E. Lizos, J.A. Murphy

Pure And Applied Chemistry

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83 Citations (Scopus)

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.

Original language	English
Pages (from-to)	117-122
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	1
Issue number	1
DOIs	https://doi.org/10.1039/b208114h
Publication status	Published - 7 Jan 2003

Keywords

formal total synthesis
oxindole alkaloids
spirotryprostain-B
radical cyclization
asymmetric nitroolefination
horsfiline

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10.1039/b208114h

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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.",

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AU - Murphy, J.A.

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N2 - 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.

AB - 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.

KW - formal total synthesis

KW - oxindole alkaloids

KW - spirotryprostain-B

KW - radical cyclization

KW - asymmetric nitroolefination

KW - horsfiline

UR - http://dx.doi.org/10.1039/b208114h

U2 - 10.1039/b208114h

DO - 10.1039/b208114h

M3 - Article

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JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 1

ER -

Concise synthesis of (±)-horsfiline and (±)-coerulescine by tandem cyclisation of iodoaryl alkenyl azides

Abstract

Keywords

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