Copper catalyzed assembly of N-aryloxazolidinones: synthesis of linezolid, tedizolid, and rivaroxaban

William Mahy; Jamie A. Leitch; Christopher G. Frost

doi:10.1002/ejoc.201600033

Copper catalyzed assembly of N-aryloxazolidinones: synthesis of linezolid, tedizolid, and rivaroxaban

William Mahy, Jamie A. Leitch, Christopher G. Frost

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

12 Citations (SciVal)

Abstract

The total synthesis of oxazolidinone-based pharmaceuticals, linezolid, tedizolid and rivaroxaban is reported. They are synthesized using a recently reported copper-catalyzed one-pot cyclization and arylation as the key step to construct the N-aryloxazolidinone core. Active pharmaceutical ingredients (API) were synthesized from a common synthetic pool of a simple protected amino alcohol in 22%, 61% and 40% total synthesis yields, respectively.

Original language	English
Pages (from-to)	1305-1313
Journal	European Journal of Organic Chemistry
Volume	2016
Issue number	7
Early online date	9 Feb 2016
DOIs	https://doi.org/10.1002/ejoc.201600033
Publication status	Published - Mar 2016

Keywords

Copper
Cross coupling
Homogeneous catalysis
Nitrogen heterocycles
Total synthesis

ASJC Scopus subject areas

Organic Chemistry
Physical and Theoretical Chemistry

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10.1002/ejoc.201600033

http://dx.doi.org/10.1002/ejoc.201600033

Cite this

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title = "Copper catalyzed assembly of N-aryloxazolidinones: synthesis of linezolid, tedizolid, and rivaroxaban",

abstract = "The total synthesis of oxazolidinone-based pharmaceuticals, linezolid, tedizolid and rivaroxaban is reported. They are synthesized using a recently reported copper-catalyzed one-pot cyclization and arylation as the key step to construct the N-aryloxazolidinone core. Active pharmaceutical ingredients (API) were synthesized from a common synthetic pool of a simple protected amino alcohol in 22%, 61% and 40% total synthesis yields, respectively.",

keywords = "Copper, Cross coupling, Homogeneous catalysis, Nitrogen heterocycles, Total synthesis",

author = "William Mahy and Leitch, {Jamie A.} and Frost, {Christopher G.}",

year = "2016",

month = mar,

doi = "10.1002/ejoc.201600033",

language = "English",

volume = "2016",

pages = "1305--1313",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "7",

}

TY - JOUR

T1 - Copper catalyzed assembly of N-aryloxazolidinones

T2 - synthesis of linezolid, tedizolid, and rivaroxaban

AU - Mahy, William

AU - Leitch, Jamie A.

AU - Frost, Christopher G.

PY - 2016/3

Y1 - 2016/3

N2 - The total synthesis of oxazolidinone-based pharmaceuticals, linezolid, tedizolid and rivaroxaban is reported. They are synthesized using a recently reported copper-catalyzed one-pot cyclization and arylation as the key step to construct the N-aryloxazolidinone core. Active pharmaceutical ingredients (API) were synthesized from a common synthetic pool of a simple protected amino alcohol in 22%, 61% and 40% total synthesis yields, respectively.

AB - The total synthesis of oxazolidinone-based pharmaceuticals, linezolid, tedizolid and rivaroxaban is reported. They are synthesized using a recently reported copper-catalyzed one-pot cyclization and arylation as the key step to construct the N-aryloxazolidinone core. Active pharmaceutical ingredients (API) were synthesized from a common synthetic pool of a simple protected amino alcohol in 22%, 61% and 40% total synthesis yields, respectively.

KW - Copper

KW - Cross coupling

KW - Homogeneous catalysis

KW - Nitrogen heterocycles

KW - Total synthesis

UR - http://www.scopus.com/inward/record.url?scp=84958817351&partnerID=8YFLogxK

UR - http://dx.doi.org/10.1002/ejoc.201600033

U2 - 10.1002/ejoc.201600033

DO - 10.1002/ejoc.201600033

M3 - Article

SN - 1434-193X

VL - 2016

SP - 1305

EP - 1313

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 7

ER -

Copper catalyzed assembly of N-aryloxazolidinones: synthesis of linezolid, tedizolid, and rivaroxaban

Abstract

Keywords

ASJC Scopus subject areas

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MC2-Mass Spectrometry (MS)

MC2- Nuclear Magnetic Resonance (NMR)

Cite this

Copper catalyzed assembly of N-aryloxazolidinones: synthesis of linezolid, tedizolid, and rivaroxaban

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Equipment

MC2-Mass Spectrometry (MS)

MC2- Nuclear Magnetic Resonance (NMR)

Cite this