The synthesis of hydroxy-pyrrolizidines and indolizidines from cyclopropenones: Towards hyacinthacines, australines and jenamidines

Vishnu V.R. Kondakal, M. Ilyas Qamar, Karl Hemming

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The reaction of cyclic imines (1-pyrrolines and piperideines) with a cyclopropenone leads to pyrrolizidines and indolizidines, respectively, each with a hydroxy group on the carbon atom at the bridgehead. The cyclopropenone functions as an all-carbon 1,3-dipole equivalent towards the cyclic imine in this reaction, and the cyclic imines used include polyhydroxylated systems, thus allowing access to australine, alexine and hyacinthacine type compounds. The pyrrolizidine products contain the core of the jenamidine and bohemamine natural products, which are of interest as cell-proliferation inhibitors and cell-cell adhesion inhibitors.

LanguageEnglish
Pages4100-4103
Number of pages4
JournalTetrahedron Letters
Volume53
Issue number32
Early online date30 May 2012
DOIs
Publication statusPublished - 8 Aug 2012

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Indolizidines
Imines
Carbon
Cell adhesion
Cell proliferation
Biological Products
Cell Adhesion
Cell Proliferation
Atoms
cyclopropenone
australine

Cite this

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title = "The synthesis of hydroxy-pyrrolizidines and indolizidines from cyclopropenones: Towards hyacinthacines, australines and jenamidines",
abstract = "The reaction of cyclic imines (1-pyrrolines and piperideines) with a cyclopropenone leads to pyrrolizidines and indolizidines, respectively, each with a hydroxy group on the carbon atom at the bridgehead. The cyclopropenone functions as an all-carbon 1,3-dipole equivalent towards the cyclic imine in this reaction, and the cyclic imines used include polyhydroxylated systems, thus allowing access to australine, alexine and hyacinthacine type compounds. The pyrrolizidine products contain the core of the jenamidine and bohemamine natural products, which are of interest as cell-proliferation inhibitors and cell-cell adhesion inhibitors.",
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The synthesis of hydroxy-pyrrolizidines and indolizidines from cyclopropenones : Towards hyacinthacines, australines and jenamidines. / Kondakal, Vishnu V.R.; Ilyas Qamar, M.; Hemming, Karl.

In: Tetrahedron Letters, Vol. 53, No. 32, 08.08.2012, p. 4100-4103.

Research output: Contribution to journalArticle

TY - JOUR

T1 - The synthesis of hydroxy-pyrrolizidines and indolizidines from cyclopropenones

T2 - Tetrahedron Letters

AU - Kondakal, Vishnu V.R.

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AU - Hemming, Karl

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AB - The reaction of cyclic imines (1-pyrrolines and piperideines) with a cyclopropenone leads to pyrrolizidines and indolizidines, respectively, each with a hydroxy group on the carbon atom at the bridgehead. The cyclopropenone functions as an all-carbon 1,3-dipole equivalent towards the cyclic imine in this reaction, and the cyclic imines used include polyhydroxylated systems, thus allowing access to australine, alexine and hyacinthacine type compounds. The pyrrolizidine products contain the core of the jenamidine and bohemamine natural products, which are of interest as cell-proliferation inhibitors and cell-cell adhesion inhibitors.

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KW - Cyclopropenone

KW - Hyacinthacine

KW - Jenamidine

KW - Pyrrolizidine and indolizidine

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