The palladium(0) Suzuki cross-coupling reaction as the key step in the synthesis of aporphinoids

R. Suau; R. Rico; F. Nájera; F. J. Ortiz-López; J. M. López-Romero; M. Moreno-Mañas; A. Roglans

doi:10.1016/j.tet.2004.05.014

The palladium(0) Suzuki cross-coupling reaction as the key step in the synthesis of aporphinoids

R. Suau, R. Rico, F. Nájera, F. J. Ortiz-López, J. M. López-Romero, M. Moreno-Mañas, A. Roglans

Department of Chemistry

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

20 Citations (Scopus)

Abstract

We report a flexible approach to the total synthesis of 4,5-dioxoaporphines based on the palladium(0) catalyzed Suzuki cross-coupling of phenylboronic acids with sterically hindered 2-bromo phenyl acetates or bromo phenyl acetamides, followed by sequential bicyclization of biarylacetamides promoted by oxalyl chloride/Lewis acid. The reduction of 4,5-dioxoaporphines provides a chemoselective entry to aporphines, dehydroaporphines and 4-hydroxy- dehydroaporphines. A three-steps total synthesis for (±)-O,O′- dimethylapomorphine from readily accessible precursors is also reported. © 2004 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	5725-5735
Journal	Tetrahedron
Volume	60
Issue number	27
DOIs	https://doi.org/10.1016/j.tet.2004.05.014
Publication status	Published - 28 Jun 2004

Keywords

4,5-Dioxoaporphine
4-Hydroxy-dehydroaporphine
Apomorphine
Aporphine
Aporphinoids
Cascade cyclization
Oxalyl chloride
Palladium
Reduction
Suzuki cross-coupling

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10.1016/j.tet.2004.05.014

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title = "The palladium(0) Suzuki cross-coupling reaction as the key step in the synthesis of aporphinoids",

abstract = "We report a flexible approach to the total synthesis of 4,5-dioxoaporphines based on the palladium(0) catalyzed Suzuki cross-coupling of phenylboronic acids with sterically hindered 2-bromo phenyl acetates or bromo phenyl acetamides, followed by sequential bicyclization of biarylacetamides promoted by oxalyl chloride/Lewis acid. The reduction of 4,5-dioxoaporphines provides a chemoselective entry to aporphines, dehydroaporphines and 4-hydroxy- dehydroaporphines. A three-steps total synthesis for (±)-O,O′- dimethylapomorphine from readily accessible precursors is also reported. {\textcopyright} 2004 Elsevier Ltd. All rights reserved.",

keywords = "4,5-Dioxoaporphine, 4-Hydroxy-dehydroaporphine, Apomorphine, Aporphine, Aporphinoids, Cascade cyclization, Oxalyl chloride, Palladium, Reduction, Suzuki cross-coupling",

author = "R. Suau and R. Rico and F. N{\'a}jera and Ortiz-L{\'o}pez, {F. J.} and L{\'o}pez-Romero, {J. M.} and M. Moreno-Ma{\~n}as and A. Roglans",

year = "2004",

month = jun,

day = "28",

doi = "10.1016/j.tet.2004.05.014",

language = "English",

volume = "60",

pages = "5725--5735",

journal = "Tetrahedron",

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TY - JOUR

T1 - The palladium(0) Suzuki cross-coupling reaction as the key step in the synthesis of aporphinoids

AU - Suau, R.

AU - Rico, R.

AU - Nájera, F.

AU - Ortiz-López, F. J.

AU - López-Romero, J. M.

AU - Moreno-Mañas, M.

AU - Roglans, A.

PY - 2004/6/28

Y1 - 2004/6/28

N2 - We report a flexible approach to the total synthesis of 4,5-dioxoaporphines based on the palladium(0) catalyzed Suzuki cross-coupling of phenylboronic acids with sterically hindered 2-bromo phenyl acetates or bromo phenyl acetamides, followed by sequential bicyclization of biarylacetamides promoted by oxalyl chloride/Lewis acid. The reduction of 4,5-dioxoaporphines provides a chemoselective entry to aporphines, dehydroaporphines and 4-hydroxy- dehydroaporphines. A three-steps total synthesis for (±)-O,O′- dimethylapomorphine from readily accessible precursors is also reported. © 2004 Elsevier Ltd. All rights reserved.

AB - We report a flexible approach to the total synthesis of 4,5-dioxoaporphines based on the palladium(0) catalyzed Suzuki cross-coupling of phenylboronic acids with sterically hindered 2-bromo phenyl acetates or bromo phenyl acetamides, followed by sequential bicyclization of biarylacetamides promoted by oxalyl chloride/Lewis acid. The reduction of 4,5-dioxoaporphines provides a chemoselective entry to aporphines, dehydroaporphines and 4-hydroxy- dehydroaporphines. A three-steps total synthesis for (±)-O,O′- dimethylapomorphine from readily accessible precursors is also reported. © 2004 Elsevier Ltd. All rights reserved.

KW - 4,5-Dioxoaporphine

KW - 4-Hydroxy-dehydroaporphine

KW - Apomorphine

KW - Aporphine

KW - Aporphinoids

KW - Cascade cyclization

KW - Oxalyl chloride

KW - Palladium

KW - Reduction

KW - Suzuki cross-coupling

U2 - 10.1016/j.tet.2004.05.014

DO - 10.1016/j.tet.2004.05.014

M3 - Article

SN - 0040-4020

VL - 60

SP - 5725

EP - 5735

JO - Tetrahedron

JF - Tetrahedron

IS - 27

ER -

The palladium(0) Suzuki cross-coupling reaction as the key step in the synthesis of aporphinoids

Abstract

Keywords

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