Synthesis of a D-ring isomer of galanthamine via a radical-based smiles rearrangement reaction

Ping Lan; Colin J. Jackson; Martin G. Banwell; Anthony C. Willis

doi:10.1021/jo501255c

Synthesis of a D-ring isomer of galanthamine via a radical-based smiles rearrangement reaction

Ping Lan
, Colin J. Jackson
, Martin G. Banwell^*
, Anthony C. Willis

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

22 Citations (Scopus)

Abstract

The 1,9-ethanoiminomethano-bridged tetrahydrodibenzo[b,d]-furan 2, a non-natural isomer of the alkaloid (-)-galanthamine (1) varying in the manner in which the D-ring is annulated to the ABC-core, has been prepared in racemic form. The synthetic sequence starts with the cyclopropane 3 and involves intramolecular Heck alkenylation and radical-based Smiles rearrangement reactions as key steps. Unlike natural product 1, but as predicted by docking studies, compound 2 is not a potent inhibitor of acetylcholine esterase.

Original language	English
Pages (from-to)	6759-6764
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	79
Issue number	14
DOIs	https://doi.org/10.1021/jo501255c
Publication status	Published - 18 Jul 2014

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title = "Synthesis of a D-ring isomer of galanthamine via a radical-based smiles rearrangement reaction",

abstract = "The 1,9-ethanoiminomethano-bridged tetrahydrodibenzo[b,d]-furan 2, a non-natural isomer of the alkaloid (-)-galanthamine (1) varying in the manner in which the D-ring is annulated to the ABC-core, has been prepared in racemic form. The synthetic sequence starts with the cyclopropane 3 and involves intramolecular Heck alkenylation and radical-based Smiles rearrangement reactions as key steps. Unlike natural product 1, but as predicted by docking studies, compound 2 is not a potent inhibitor of acetylcholine esterase.",

author = "Ping Lan and Jackson, \{Colin J.\} and Banwell, \{Martin G.\} and Willis, \{Anthony C.\}",

year = "2014",

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AU - Jackson, Colin J.

AU - Banwell, Martin G.

AU - Willis, Anthony C.

PY - 2014/7/18

Y1 - 2014/7/18

N2 - The 1,9-ethanoiminomethano-bridged tetrahydrodibenzo[b,d]-furan 2, a non-natural isomer of the alkaloid (-)-galanthamine (1) varying in the manner in which the D-ring is annulated to the ABC-core, has been prepared in racemic form. The synthetic sequence starts with the cyclopropane 3 and involves intramolecular Heck alkenylation and radical-based Smiles rearrangement reactions as key steps. Unlike natural product 1, but as predicted by docking studies, compound 2 is not a potent inhibitor of acetylcholine esterase.

AB - The 1,9-ethanoiminomethano-bridged tetrahydrodibenzo[b,d]-furan 2, a non-natural isomer of the alkaloid (-)-galanthamine (1) varying in the manner in which the D-ring is annulated to the ABC-core, has been prepared in racemic form. The synthetic sequence starts with the cyclopropane 3 and involves intramolecular Heck alkenylation and radical-based Smiles rearrangement reactions as key steps. Unlike natural product 1, but as predicted by docking studies, compound 2 is not a potent inhibitor of acetylcholine esterase.

UR - https://www.scopus.com/pages/publications/84904565728

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DO - 10.1021/jo501255c

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 14

ER -

Synthesis of a D-ring isomer of galanthamine via a radical-based smiles rearrangement reaction

Abstract

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