Synthesis of polycyclic alkaloid-type compounds by an N -acyliminium Pictet-Spengler/diels-alder sequence

Eelco Ruijter; Jaime Garcia-Hartjes; Frank Hoffmann; Loek T.M. Vanwandelen; Frans J.J. Dekanter; Elwin Janssen; Romano V.A. Orru

doi:10.1055/s-0030-1258057

Synthesis of polycyclic alkaloid-type compounds by an N -acyliminium Pictet-Spengler/diels-alder sequence

Eelco Ruijter, Jaime Garcia-Hartjes, Frank Hoffmann, Loek T.M. Vanwandelen, Frans J.J. Dekanter, Elwin Janssen, Romano V.A. Orru

Research output: Contribution to Journal › Article › Academic › peer-review

Abstract

A range of structurally diverse penta- and hexacyclic alkaloid-type compounds have been prepared in a two-step procedure from readily available starting materials. A flexible N-acyliminium Pictet-Spengler reaction employing electron-rich -arylethyl-amines, cinnamaldehyde derivatives, and alkynoyl chlorides sets the stage for an intramolecular Diels-Alder cycloaddition. The complex and diverse polycyclic alkaloid-like compounds are easily obtained in reasonable to excellent yield in a reliable and efficient reaction sequence. © Georg Thieme Verlag Stuttgart New York.

Original language	English
Pages (from-to)	2485-2489
Number of pages	5
Journal	Synlett
Volume	2010
Issue number	16
Early online date	19 Aug 2010
DOIs	https://doi.org/10.1055/s-0030-1258057
Publication status	Published - Oct 2010

Keywords

Diels-Alder reactions
N -acyliminium Pictet-Spengler Reactions
alkaloids
microwave irradiation
polycycles

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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title = "Synthesis of polycyclic alkaloid-type compounds by an N -acyliminium Pictet-Spengler/diels-alder sequence",

abstract = "A range of structurally diverse penta- and hexacyclic alkaloid-type compounds have been prepared in a two-step procedure from readily available starting materials. A flexible N-acyliminium Pictet-Spengler reaction employing electron-rich -arylethyl-amines, cinnamaldehyde derivatives, and alkynoyl chlorides sets the stage for an intramolecular Diels-Alder cycloaddition. The complex and diverse polycyclic alkaloid-like compounds are easily obtained in reasonable to excellent yield in a reliable and efficient reaction sequence. {\textcopyright} Georg Thieme Verlag Stuttgart New York.",

keywords = "Diels-Alder reactions, N -acyliminium Pictet-Spengler Reactions, alkaloids, microwave irradiation, polycycles",

author = "Eelco Ruijter and Jaime Garcia-Hartjes and Frank Hoffmann and Vanwandelen, {Loek T.M.} and Dekanter, {Frans J.J.} and Elwin Janssen and Orru, {Romano V.A.}",

year = "2010",

month = oct,

doi = "10.1055/s-0030-1258057",

language = "English",

volume = "2010",

pages = "2485--2489",

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issn = "0936-5214",

publisher = "Georg Thieme Verlag",

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T1 - Synthesis of polycyclic alkaloid-type compounds by an N -acyliminium Pictet-Spengler/diels-alder sequence

AU - Ruijter, Eelco

AU - Garcia-Hartjes, Jaime

AU - Hoffmann, Frank

AU - Vanwandelen, Loek T.M.

AU - Dekanter, Frans J.J.

AU - Janssen, Elwin

AU - Orru, Romano V.A.

PY - 2010/10

Y1 - 2010/10

N2 - A range of structurally diverse penta- and hexacyclic alkaloid-type compounds have been prepared in a two-step procedure from readily available starting materials. A flexible N-acyliminium Pictet-Spengler reaction employing electron-rich -arylethyl-amines, cinnamaldehyde derivatives, and alkynoyl chlorides sets the stage for an intramolecular Diels-Alder cycloaddition. The complex and diverse polycyclic alkaloid-like compounds are easily obtained in reasonable to excellent yield in a reliable and efficient reaction sequence. © Georg Thieme Verlag Stuttgart New York.

AB - A range of structurally diverse penta- and hexacyclic alkaloid-type compounds have been prepared in a two-step procedure from readily available starting materials. A flexible N-acyliminium Pictet-Spengler reaction employing electron-rich -arylethyl-amines, cinnamaldehyde derivatives, and alkynoyl chlorides sets the stage for an intramolecular Diels-Alder cycloaddition. The complex and diverse polycyclic alkaloid-like compounds are easily obtained in reasonable to excellent yield in a reliable and efficient reaction sequence. © Georg Thieme Verlag Stuttgart New York.

KW - Diels-Alder reactions

KW - N -acyliminium Pictet-Spengler Reactions

KW - alkaloids

KW - microwave irradiation

KW - polycycles

U2 - 10.1055/s-0030-1258057

DO - 10.1055/s-0030-1258057

M3 - Article

SN - 0936-5214

VL - 2010

SP - 2485

EP - 2489

JO - Synlett

JF - Synlett

IS - 16

ER -

Synthesis of polycyclic alkaloid-type compounds by an N -acyliminium Pictet-Spengler/diels-alder sequence

Abstract

Keywords

UN SDGs

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