Total synthesis of (+)-pleuromutilin

Neal J. Fazakerley; Matthew D. Helm; David J. Procter

doi:10.1002/chem.201300968

Total synthesis of (+)-pleuromutilin

Neal J. Fazakerley, Matthew D. Helm, David J. Procter

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

Abstract

The first enantiospecific total synthesis of the antibacterial natural product (+)-pleuromutilin has been achieved. The approach includes the synthesis of a non-racemic cyclisation substrate from (+)-trans-dihydrocarvone, a highly selective SmI2-mediated cyclisation cascade, an electron transfer reduction of a hindered ester, and the first efficient conversion of (+)-mutilin to the target. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Original language	English
Pages (from-to)	6718-6723
Number of pages	5
Journal	Chemistry - A European Journal
Volume	19
Issue number	21
DOIs	https://doi.org/10.1002/chem.201300968
Publication status	Published - 17 May 2013

Keywords

natural products
pleuromutilin
radicals
samarium
total synthesis

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10.1002/chem.201300968

CCDC 913369: Experimental Crystal Structure Determination
Fazakerley, N. (Contributor), Helm, M. D. (Contributor) & Procter, D. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2013
DOI: 10.5517/ccznfjk, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccznfjk&sid=DataCite
Dataset

Cite this

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title = "Total synthesis of (+)-pleuromutilin",

abstract = "The first enantiospecific total synthesis of the antibacterial natural product (+)-pleuromutilin has been achieved. The approach includes the synthesis of a non-racemic cyclisation substrate from (+)-trans-dihydrocarvone, a highly selective SmI2-mediated cyclisation cascade, an electron transfer reduction of a hindered ester, and the first efficient conversion of (+)-mutilin to the target. Copyright {\textcopyright} 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

keywords = "natural products, pleuromutilin, radicals, samarium, total synthesis",

author = "Fazakerley, {Neal J.} and Helm, {Matthew D.} and Procter, {David J.}",

year = "2013",

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doi = "10.1002/chem.201300968",

language = "English",

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T1 - Total synthesis of (+)-pleuromutilin

AU - Fazakerley, Neal J.

AU - Helm, Matthew D.

AU - Procter, David J.

PY - 2013/5/17

Y1 - 2013/5/17

N2 - The first enantiospecific total synthesis of the antibacterial natural product (+)-pleuromutilin has been achieved. The approach includes the synthesis of a non-racemic cyclisation substrate from (+)-trans-dihydrocarvone, a highly selective SmI2-mediated cyclisation cascade, an electron transfer reduction of a hindered ester, and the first efficient conversion of (+)-mutilin to the target. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

AB - The first enantiospecific total synthesis of the antibacterial natural product (+)-pleuromutilin has been achieved. The approach includes the synthesis of a non-racemic cyclisation substrate from (+)-trans-dihydrocarvone, a highly selective SmI2-mediated cyclisation cascade, an electron transfer reduction of a hindered ester, and the first efficient conversion of (+)-mutilin to the target. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

KW - natural products

KW - pleuromutilin

KW - radicals

KW - samarium

KW - total synthesis

U2 - 10.1002/chem.201300968

DO - 10.1002/chem.201300968

M3 - Article

SN - 0947-6539

VL - 19

SP - 6718

EP - 6723

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 21

ER -

Total synthesis of (+)-pleuromutilin

Abstract

Keywords

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Datasets

CCDC 913369: Experimental Crystal Structure Determination

Cite this