Total synthesis of (±)-isophellibiline

Raymond L. Funk; Johannes Belmar

doi:10.1016/j.tetlet.2011.10.161

Total synthesis of (±)-isophellibiline

Raymond L. Funk, Johannes Belmar

Chemistry

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

11 Scopus citations

Abstract

The total synthesis of (±)-isophellibiline is described. This represents the first synthesis of a member of the nonaromatic homoerythrinan family of alkaloids. The tetracyclic ring system of the natural product was quickly assembled by a strategy that features a retrocycloaddition/cycloaddition reaction of amidodioxin, an intramolecular Heck reaction and a 6π-electrocyclic ring closure of a dienoic acid.

Original language	English (US)
Pages (from-to)	176-178
Number of pages	3
Journal	Tetrahedron Letters
Volume	53
Issue number	2
DOIs	https://doi.org/10.1016/j.tetlet.2011.10.161
State	Published - Jan 11 2012

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2011.10.161

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title = "Total synthesis of (±)-isophellibiline",

abstract = "The total synthesis of (±)-isophellibiline is described. This represents the first synthesis of a member of the nonaromatic homoerythrinan family of alkaloids. The tetracyclic ring system of the natural product was quickly assembled by a strategy that features a retrocycloaddition/cycloaddition reaction of amidodioxin, an intramolecular Heck reaction and a 6π-electrocyclic ring closure of a dienoic acid.",

author = "Funk, {Raymond L.} and Johannes Belmar",

note = "Funding Information: We thank Dr. Nicole Langlois 20 for spectra of authentic isophellibiline. We appreciate the financial support provided by the National Institute of Health ( GM28663 ). ",

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T1 - Total synthesis of (±)-isophellibiline

AU - Funk, Raymond L.

AU - Belmar, Johannes

N1 - Funding Information: We thank Dr. Nicole Langlois 20 for spectra of authentic isophellibiline. We appreciate the financial support provided by the National Institute of Health ( GM28663 ).

PY - 2012/1/11

Y1 - 2012/1/11

N2 - The total synthesis of (±)-isophellibiline is described. This represents the first synthesis of a member of the nonaromatic homoerythrinan family of alkaloids. The tetracyclic ring system of the natural product was quickly assembled by a strategy that features a retrocycloaddition/cycloaddition reaction of amidodioxin, an intramolecular Heck reaction and a 6π-electrocyclic ring closure of a dienoic acid.

AB - The total synthesis of (±)-isophellibiline is described. This represents the first synthesis of a member of the nonaromatic homoerythrinan family of alkaloids. The tetracyclic ring system of the natural product was quickly assembled by a strategy that features a retrocycloaddition/cycloaddition reaction of amidodioxin, an intramolecular Heck reaction and a 6π-electrocyclic ring closure of a dienoic acid.

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DO - 10.1016/j.tetlet.2011.10.161

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 2

ER -

Total synthesis of (±)-isophellibiline

Abstract

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