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

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

doi:10.1021/ol300039x

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

Richard G. Doveston, Rene Steendam, Stuart Jones, Richard J. K. Taylor

Chemistry

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

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
DOIs	https://doi.org/10.1021/ol300039x
Publication status	Published - 17 Feb 2012

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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.",

author = "Doveston, {Richard G.} and Rene Steendam and Stuart Jones and Taylor, {Richard J. K.}",

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AU - Doveston, Richard G.

AU - Steendam, Rene

AU - Jones, Stuart

AU - Taylor, Richard J. K.

PY - 2012/2/17

Y1 - 2012/2/17

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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.

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EP - 1125

JO - Organic Letters

JF - Organic Letters

IS - 4

ER -

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

Abstract

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