Asymmetric synthesis of synthetic alkaloids by a tandem biocatalysis/Ugi/Pictet-Spengler-type cyclization sequence

Anass Znabet; Job Zonneveld; Elwin Janssen; Frans J J De Kanter; Madeleine Helliwell; Nicholas J Turner; Eelco Ruijter; Romano V A Orru

doi:10.1039/c0cc02938f

Asymmetric synthesis of synthetic alkaloids by a tandem biocatalysis/Ugi/Pictet-Spengler-type cyclization sequence

Anass Znabet
, Job Zonneveld
, Elwin Janssen
, Frans J J De Kanter
, Madeleine Helliwell
, Nicholas J Turner
, Eelco Ruijter
, Romano V A Orru

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

Abstract

We have combined the biocatalytic desymmetrization of 3,4-cis-substituted meso-pyrrolidines with an Ugi-type multicomponent reaction followed in situ by a Pictet-Spengler-type cyclization reaction sequence for the rapid asymmetric synthesis of alkaloid-like polycyclic compounds.

Original language	English
Pages (from-to)	7706-7708
Number of pages	3
Journal	Chemical Commununications
Volume	46
Issue number	41
Early online date	27 Sept 2010
DOIs	https://doi.org/10.1039/c0cc02938f
Publication status	Published - 7 Nov 2010

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SDG 6 Clean Water and Sanitation

Keywords

Alkaloids/biosynthesis
Aspergillus niger/enzymology
Biocatalysis
Cyclization
Monoamine Oxidase/metabolism
Oxidation-Reduction
Stereoisomerism
Substrate Specificity

Access to Document

10.1039/c0cc02938f

Persistent URL (handle)

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CCDC 786098: Experimental Crystal Structure Determination
Znabet, A. (Contributor), Zonneveld, J. (Contributor), Janssen, E. (Contributor), De Kanter, F. J. J. (Contributor), Helliwell, M. (Contributor), Turner, N. J. (Contributor), Ruijter, E. (Contributor) & Orru, R. V. A. (Contributor), Unknown, 1 Jan 2011
DOI: 10.5517/ccvd007, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccvd007&sid=DataCite
Dataset / Software: Dataset

Cite this

@article{e11209dafa9e4e49bb39d42e751dc6ef,

title = "Asymmetric synthesis of synthetic alkaloids by a tandem biocatalysis/Ugi/Pictet-Spengler-type cyclization sequence",

abstract = "We have combined the biocatalytic desymmetrization of 3,4-cis-substituted meso-pyrrolidines with an Ugi-type multicomponent reaction followed in situ by a Pictet-Spengler-type cyclization reaction sequence for the rapid asymmetric synthesis of alkaloid-like polycyclic compounds.",

keywords = "Alkaloids/biosynthesis, Aspergillus niger/enzymology, Biocatalysis, Cyclization, Monoamine Oxidase/metabolism, Oxidation-Reduction, Stereoisomerism, Substrate Specificity",

author = "Anass Znabet and Job Zonneveld and Elwin Janssen and \{De Kanter\}, \{Frans J J\} and Madeleine Helliwell and Turner, \{Nicholas J\} and Eelco Ruijter and Orru, \{Romano V A\}",

year = "2010",

month = nov,

day = "7",

doi = "10.1039/c0cc02938f",

language = "English",

volume = "46",

pages = "7706--7708",

journal = "Chemical Commununications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "41",

}

TY - JOUR

T1 - Asymmetric synthesis of synthetic alkaloids by a tandem biocatalysis/Ugi/Pictet-Spengler-type cyclization sequence

AU - Znabet, Anass

AU - Zonneveld, Job

AU - Janssen, Elwin

AU - De Kanter, Frans J J

AU - Helliwell, Madeleine

AU - Turner, Nicholas J

AU - Ruijter, Eelco

AU - Orru, Romano V A

PY - 2010/11/7

Y1 - 2010/11/7

N2 - We have combined the biocatalytic desymmetrization of 3,4-cis-substituted meso-pyrrolidines with an Ugi-type multicomponent reaction followed in situ by a Pictet-Spengler-type cyclization reaction sequence for the rapid asymmetric synthesis of alkaloid-like polycyclic compounds.

AB - We have combined the biocatalytic desymmetrization of 3,4-cis-substituted meso-pyrrolidines with an Ugi-type multicomponent reaction followed in situ by a Pictet-Spengler-type cyclization reaction sequence for the rapid asymmetric synthesis of alkaloid-like polycyclic compounds.

KW - Alkaloids/biosynthesis

KW - Aspergillus niger/enzymology

KW - Biocatalysis

KW - Cyclization

KW - Monoamine Oxidase/metabolism

KW - Oxidation-Reduction

KW - Stereoisomerism

KW - Substrate Specificity

U2 - 10.1039/c0cc02938f

DO - 10.1039/c0cc02938f

M3 - Article

C2 - 20871902

SN - 1359-7345

VL - 46

SP - 7706

EP - 7708

JO - Chemical Commununications

JF - Chemical Commununications

IS - 41

ER -

Asymmetric synthesis of synthetic alkaloids by a tandem biocatalysis/Ugi/Pictet-Spengler-type cyclization sequence

Abstract

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Keywords

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Datasets

CCDC 786098: Experimental Crystal Structure Determination

Cite this