Ravynic acid, an antibiotic polyeneyne tetramic acid from Penicillium sp. elucidated through synthesis

Jonathan D. Myrtle; Andrew M. Beekman; Russell A. Barrow

doi:10.1039/C6OB00938G

Ravynic acid, an antibiotic polyeneyne tetramic acid from Penicillium sp. elucidated through synthesis

Jonathan D. Myrtle, Andrew M. Beekman, Russell A. Barrow

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

12 Citations (Scopus)

Abstract

A new antibiotic natural product, ravynic acid, has been isolated from a Penicillium sp. of fungus, collected from Ravensbourne National Park. The 3-acylpolyenyne tetramic acid structure was definitively elucidated via synthesis. Highlights of the synthetic method include the heat induced formation of the 3-acylphosphorane tetramic acid and a selective Wittig cross-coupling to efficiently prepare the natural compounds carbon skeleton. The natural compound was shown to inhibit the growth of Staphylococcus aureus down to concentrations of 2.5 µg mL−1.

Original language	English
Pages (from-to)	8253-8260
Number of pages	8
Journal	Organic & Biomolecular Chemistry
Volume	14
Issue number	35
DOIs	https://doi.org/10.1039/C6OB00938G
Publication status	Published - 21 Jul 2016

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10.1039/C6OB00938G

Cite this

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title = "Ravynic acid, an antibiotic polyeneyne tetramic acid from Penicillium sp. elucidated through synthesis",

abstract = "A new antibiotic natural product, ravynic acid, has been isolated from a Penicillium sp. of fungus, collected from Ravensbourne National Park. The 3-acylpolyenyne tetramic acid structure was definitively elucidated via synthesis. Highlights of the synthetic method include the heat induced formation of the 3-acylphosphorane tetramic acid and a selective Wittig cross-coupling to efficiently prepare the natural compounds carbon skeleton. The natural compound was shown to inhibit the growth of Staphylococcus aureus down to concentrations of 2.5 µg mL−1.",

author = "Myrtle, {Jonathan D.} and Beekman, {Andrew M.} and Barrow, {Russell A.}",

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AU - Myrtle, Jonathan D.

AU - Beekman, Andrew M.

AU - Barrow, Russell A.

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N2 - A new antibiotic natural product, ravynic acid, has been isolated from a Penicillium sp. of fungus, collected from Ravensbourne National Park. The 3-acylpolyenyne tetramic acid structure was definitively elucidated via synthesis. Highlights of the synthetic method include the heat induced formation of the 3-acylphosphorane tetramic acid and a selective Wittig cross-coupling to efficiently prepare the natural compounds carbon skeleton. The natural compound was shown to inhibit the growth of Staphylococcus aureus down to concentrations of 2.5 µg mL−1.

AB - A new antibiotic natural product, ravynic acid, has been isolated from a Penicillium sp. of fungus, collected from Ravensbourne National Park. The 3-acylpolyenyne tetramic acid structure was definitively elucidated via synthesis. Highlights of the synthetic method include the heat induced formation of the 3-acylphosphorane tetramic acid and a selective Wittig cross-coupling to efficiently prepare the natural compounds carbon skeleton. The natural compound was shown to inhibit the growth of Staphylococcus aureus down to concentrations of 2.5 µg mL−1.

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DO - 10.1039/C6OB00938G

M3 - Article

VL - 14

SP - 8253

EP - 8260

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

SN - 1477-0520

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