A strategic approach to [6,6]-bicyclic lactones: application towards the CD fragment of DHβE

Tue Heesgaard Jepsen; Emil Glibstrup; Francois Louis Jean Crestey; Anders A. Jensen; Jesper Langgaard Kristensen

doi:10.3762/bjoc.13.98

A strategic approach to [6,6]-bicyclic lactones: application towards the CD fragment of DHβE

Tue Heesgaard Jepsen, Emil Glibstrup, Francois Louis Jean Crestey, Anders A. Jensen, Jesper Langgaard Kristensen

Department of Chemistry

5 Citations (Scopus)

126 Downloads (Pure)

Abstract

We report an effective synthetic protocol to access [6,6]-bicyclic lactone moieties through a regio- and stereoselective intramolecular Mizoroki–Heck cross-coupling reaction followed by a 6π-electrocyclization. This method enabled the first synthesis of the elusive CD fragment of the Erythrina alkaloid DHβE. Preliminary pharmacological evaluations support the notion that the key pharmacophores of DHβE are located in the A and B rings.

Original language	English
Journal	Beilstein Journal of Organic Chemistry
Volume	13
Pages (from-to)	988-994
Number of pages	7
ISSN	2195-951X
DOIs	https://doi.org/10.3762/bjoc.13.98
Publication status	Published - 22 May 2017

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10.3762/bjoc.13.98Licence: CC BY

A strategic approach to 6,6 bicyclic lactonesFinal published version, 618 KBLicence: CC BY

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abstract = "We report an effective synthetic protocol to access [6,6]-bicyclic lactone moieties through a regio- and stereoselective intramolecular Mizoroki–Heck cross-coupling reaction followed by a 6π-electrocyclization. This method enabled the first synthesis of the elusive CD fragment of the Erythrina alkaloid DHβE. Preliminary pharmacological evaluations support the notion that the key pharmacophores of DHβE are located in the A and B rings.",

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AU - Jepsen, Tue Heesgaard

AU - Glibstrup, Emil

AU - Crestey, Francois Louis Jean

AU - Jensen, Anders A.

AU - Kristensen, Jesper Langgaard

PY - 2017/5/22

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AB - We report an effective synthetic protocol to access [6,6]-bicyclic lactone moieties through a regio- and stereoselective intramolecular Mizoroki–Heck cross-coupling reaction followed by a 6π-electrocyclization. This method enabled the first synthesis of the elusive CD fragment of the Erythrina alkaloid DHβE. Preliminary pharmacological evaluations support the notion that the key pharmacophores of DHβE are located in the A and B rings.

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DO - 10.3762/bjoc.13.98

M3 - Journal article

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EP - 994

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

A strategic approach to [6,6]-bicyclic lactones: application towards the CD fragment of DHβE

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