Synthesis of the heterocyclic core of martinelline and martinellic acid

Mark Hadden; Mark Nieuwenhuyzen; Daire Osborne; Paul J. Stevenson; Norris Thompson; Andrew D. Walker

doi:10.1016/j.tet.2006.02.029

Synthesis of the heterocyclic core of martinelline and martinellic acid

Mark Hadden, Mark Nieuwenhuyzen, Daire Osborne, Paul J. Stevenson^*, Norris Thompson, Andrew D. Walker

^*Corresponding author for this work

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

58 Citations (Scopus)

Abstract

A Povarov reaction, between an aromatic imine derived from cinnamaldehyde and a cyclic enamide, was employed to rapidly construct the tricyclic core of the alkaloids martinelline and martinellic acid. The cycloaddition was completely regioselective though the exo/endo selectivity was poor. The diastereoisomers were readily separated by flash chromatography and the relative stereochemistry of the exo-isomer confirmed by single crystal X-ray crystallography. This intermediate was converted to the central core of the aforementioned alkaloids in five additional synthetic operations.

Original language	English
Pages (from-to)	3977-3984
Number of pages	8
Journal	Tetrahedron
Volume	62
Issue number	17
DOIs	https://doi.org/10.1016/j.tet.2006.02.029
Publication status	Published - 24 Apr 2006

Keywords

Alkaloid
Imino Diels-Alder
Lewis acid catalysis
Martinellic acid
Martinelline
Povarov reaction

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2006.02.029

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title = "Synthesis of the heterocyclic core of martinelline and martinellic acid",

abstract = "A Povarov reaction, between an aromatic imine derived from cinnamaldehyde and a cyclic enamide, was employed to rapidly construct the tricyclic core of the alkaloids martinelline and martinellic acid. The cycloaddition was completely regioselective though the exo/endo selectivity was poor. The diastereoisomers were readily separated by flash chromatography and the relative stereochemistry of the exo-isomer confirmed by single crystal X-ray crystallography. This intermediate was converted to the central core of the aforementioned alkaloids in five additional synthetic operations.",

keywords = "Alkaloid, Imino Diels-Alder, Lewis acid catalysis, Martinellic acid, Martinelline, Povarov reaction",

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T1 - Synthesis of the heterocyclic core of martinelline and martinellic acid

AU - Hadden, Mark

AU - Nieuwenhuyzen, Mark

AU - Osborne, Daire

AU - Stevenson, Paul J.

AU - Thompson, Norris

AU - Walker, Andrew D.

PY - 2006/4/24

Y1 - 2006/4/24

N2 - A Povarov reaction, between an aromatic imine derived from cinnamaldehyde and a cyclic enamide, was employed to rapidly construct the tricyclic core of the alkaloids martinelline and martinellic acid. The cycloaddition was completely regioselective though the exo/endo selectivity was poor. The diastereoisomers were readily separated by flash chromatography and the relative stereochemistry of the exo-isomer confirmed by single crystal X-ray crystallography. This intermediate was converted to the central core of the aforementioned alkaloids in five additional synthetic operations.

AB - A Povarov reaction, between an aromatic imine derived from cinnamaldehyde and a cyclic enamide, was employed to rapidly construct the tricyclic core of the alkaloids martinelline and martinellic acid. The cycloaddition was completely regioselective though the exo/endo selectivity was poor. The diastereoisomers were readily separated by flash chromatography and the relative stereochemistry of the exo-isomer confirmed by single crystal X-ray crystallography. This intermediate was converted to the central core of the aforementioned alkaloids in five additional synthetic operations.

KW - Alkaloid

KW - Imino Diels-Alder

KW - Lewis acid catalysis

KW - Martinellic acid

KW - Martinelline

KW - Povarov reaction

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DO - 10.1016/j.tet.2006.02.029

M3 - Article

AN - SCOPUS:33645959843

VL - 62

SP - 3977

EP - 3984

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 17

ER -

Synthesis of the heterocyclic core of martinelline and martinellic acid

Abstract

Keywords

ASJC Scopus subject areas

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