Total synthesis of an oxepine natural product, (±)-janoxepin

Richard G. Doveston; René Steendam; Stuart Jones; Richard J K Taylor

doi:10.1021/ol300039x

Total synthesis of an oxepine natural product, (±)-janoxepin

Richard G. Doveston, René Steendam, Stuart Jones, Richard J K Taylor^*

^*Corresponding author for this work

Strathclyde Institute Of Pharmacy And Biomedical Sciences

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

41 Citations (Scopus)

Abstract

The total synthesis of (±)-janoxepin, a novel antiplasmodial d-leucine derived oxepine-pyrimidinone-ketopiperazine isolated from the fungus Aspergillus janus, is described. The cornerstones of the synthetic route are pyrimidinone preparation, ring-closing metathesis, aldol introduction of the enamide, and dihydro-oxepine elaboration. This synthetic route proved very efficient for the formation of a number of janoxepin analogues, including dihydro-janoxepin and tetrahydro-janoxepin.

Original language	English
Pages (from-to)	1122-1125
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	4
Early online date	30 Jan 2012
DOIs	https://doi.org/10.1021/ol300039x
Publication status	Published - 17 Feb 2012

Keywords

oxepine
janoxepin
Aspergillus janus

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10.1021/ol300039x

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abstract = "The total synthesis of (±)-janoxepin, a novel antiplasmodial d-leucine derived oxepine-pyrimidinone-ketopiperazine isolated from the fungus Aspergillus janus, is described. The cornerstones of the synthetic route are pyrimidinone preparation, ring-closing metathesis, aldol introduction of the enamide, and dihydro-oxepine elaboration. This synthetic route proved very efficient for the formation of a number of janoxepin analogues, including dihydro-janoxepin and tetrahydro-janoxepin. ",

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T1 - Total synthesis of an oxepine natural product, (±)-janoxepin

AU - Doveston, Richard G.

AU - Steendam, René

AU - Jones, Stuart

AU - Taylor, Richard J K

PY - 2012/2/17

Y1 - 2012/2/17

N2 - The total synthesis of (±)-janoxepin, a novel antiplasmodial d-leucine derived oxepine-pyrimidinone-ketopiperazine isolated from the fungus Aspergillus janus, is described. The cornerstones of the synthetic route are pyrimidinone preparation, ring-closing metathesis, aldol introduction of the enamide, and dihydro-oxepine elaboration. This synthetic route proved very efficient for the formation of a number of janoxepin analogues, including dihydro-janoxepin and tetrahydro-janoxepin.

AB - The total synthesis of (±)-janoxepin, a novel antiplasmodial d-leucine derived oxepine-pyrimidinone-ketopiperazine isolated from the fungus Aspergillus janus, is described. The cornerstones of the synthetic route are pyrimidinone preparation, ring-closing metathesis, aldol introduction of the enamide, and dihydro-oxepine elaboration. This synthetic route proved very efficient for the formation of a number of janoxepin analogues, including dihydro-janoxepin and tetrahydro-janoxepin.

KW - oxepine

KW - janoxepin

KW - Aspergillus janus

UR - http://www.scopus.com/inward/record.url?scp=84857200734&partnerID=8YFLogxK

U2 - 10.1021/ol300039x

DO - 10.1021/ol300039x

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AN - SCOPUS:84857200734

SN - 1523-7060

VL - 14

SP - 1122

EP - 1125

JO - Organic Letters

JF - Organic Letters

IS - 4

ER -

Total synthesis of an oxepine natural product, (±)-janoxepin

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Keywords

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