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

D.E. Lizos, J.A. Murphy

Research output: Contribution to journalArticle

72 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.
LanguageEnglish
Pages117-122
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume1
Issue number1
DOIs
Publication statusPublished - 7 Jan 2003

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Azides
Cyclization
synthesis
acids
4-anisidine
3-iodoaniline
horsfiline
coerulescine
itaconic acid

Keywords

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

Cite this

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keywords = "formal total synthesis, oxindole alkaloids, spirotryprostain-B, radical cyclization, asymmetric nitroolefination, horsfiline",
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Concise synthesis of (±)-horsfiline and (±)-coerulescine by tandem cyclisation of iodoaryl alkenyl azides. / Lizos, D.E.; Murphy, J.A.

In: Organic and Biomolecular Chemistry, Vol. 1, No. 1, 07.01.2003, p. 117-122.

Research output: Contribution to journalArticle

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AU - Murphy, J.A.

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KW - formal total synthesis

KW - oxindole alkaloids

KW - spirotryprostain-B

KW - radical cyclization

KW - asymmetric nitroolefination

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