A cross-metathesis approach to novel pantothenamide derivatives

Jinming Guan; Matthew Hachey; Lekha Puri; Vanessa Howieson; Kevin J. Saliba; Karine Auclair

doi:10.3762/bjoc.12.95

A cross-metathesis approach to novel pantothenamide derivatives

Jinming Guan, Matthew Hachey, Lekha Puri, Vanessa Howieson, Kevin J. Saliba, Karine Auclair^*

^*Corresponding author for this work

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

15 Citations (Scopus)

Abstract

Pantothenamides are known for their in vitro antimicrobial activity. Our group has previously reported a new stereoselective route to access derivatives modified at the geminal dimethyl moiety. This route however fails in the addition of large substituents. Here we report a new synthetic route that exploits the known allyl derivative, allowing for the installation of larger groups via cross-metathesis. The method was applied in the synthesis of a new pantothenamide with improved stability in human blood.

Original language	English
Pages (from-to)	963-968
Number of pages	6
Journal	Beilstein Journal of Organic Chemistry
Volume	12
DOIs	https://doi.org/10.3762/bjoc.12.95
Publication status	Published - 13 May 2016

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title = "A cross-metathesis approach to novel pantothenamide derivatives",

abstract = "Pantothenamides are known for their in vitro antimicrobial activity. Our group has previously reported a new stereoselective route to access derivatives modified at the geminal dimethyl moiety. This route however fails in the addition of large substituents. Here we report a new synthetic route that exploits the known allyl derivative, allowing for the installation of larger groups via cross-metathesis. The method was applied in the synthesis of a new pantothenamide with improved stability in human blood.",

keywords = "Antibiotic, Antiplasmodial, Coenzyme A, Metathesis, Pantothenate",

author = "Jinming Guan and Matthew Hachey and Lekha Puri and Vanessa Howieson and Saliba, \{Kevin J.\} and Karine Auclair",

note = "Publisher Copyright: {\textcopyright} 2016 Guan et al; licensee Beilstein-Institut.",

year = "2016",

month = may,

day = "13",

doi = "10.3762/bjoc.12.95",

language = "English",

volume = "12",

pages = "963--968",

journal = "Beilstein Journal of Organic Chemistry",

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TY - JOUR

T1 - A cross-metathesis approach to novel pantothenamide derivatives

AU - Guan, Jinming

AU - Hachey, Matthew

AU - Puri, Lekha

AU - Howieson, Vanessa

AU - Saliba, Kevin J.

AU - Auclair, Karine

PY - 2016/5/13

Y1 - 2016/5/13

N2 - Pantothenamides are known for their in vitro antimicrobial activity. Our group has previously reported a new stereoselective route to access derivatives modified at the geminal dimethyl moiety. This route however fails in the addition of large substituents. Here we report a new synthetic route that exploits the known allyl derivative, allowing for the installation of larger groups via cross-metathesis. The method was applied in the synthesis of a new pantothenamide with improved stability in human blood.

AB - Pantothenamides are known for their in vitro antimicrobial activity. Our group has previously reported a new stereoselective route to access derivatives modified at the geminal dimethyl moiety. This route however fails in the addition of large substituents. Here we report a new synthetic route that exploits the known allyl derivative, allowing for the installation of larger groups via cross-metathesis. The method was applied in the synthesis of a new pantothenamide with improved stability in human blood.

KW - Antibiotic

KW - Antiplasmodial

KW - Coenzyme A

KW - Metathesis

KW - Pantothenate

UR - https://www.scopus.com/pages/publications/84975832640

U2 - 10.3762/bjoc.12.95

DO - 10.3762/bjoc.12.95

M3 - Article

SN - 1860-5397

VL - 12

SP - 963

EP - 968

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

A cross-metathesis approach to novel pantothenamide derivatives

Abstract

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