A Second-Generation Chemoenzymatic Total Synthesis of Platencin

Muhammad Rehmani N.; Draffan Alistair G.; Banwell Martin G.; Willis Anthony C.

doi:10.1055/s-0035-1560814

A Second-Generation Chemoenzymatic Total Synthesis of Platencin

Muhammad Rehmani N., Draffan Alistair G., Banwell Martin G.^*, Willis Anthony C.

^*Corresponding author for this work

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

2 Citations (Scopus)

Abstract

A total synthesis of the potent antibacterial agent platencin is described. The reaction sequence used involves, as starting material, an enantiomerically pure cis-1,2-dihydrocatechol derived from the whole-cell biotransformation of iodobenzene. Simple chemical manipulations of this metabolite provide a triene that engages in a thermally promoted intramolecular Diels–Alder reaction to establish the octahydro-2H-2,4a-ethanonaphthalene core of platencin.

Original language	English
Article number	st-2015-d0783-l
Pages (from-to)	61-66
Number of pages	6
Journal	Synlett
Volume	27
Issue number	1
DOIs	https://doi.org/10.1055/s-0035-1560814
Publication status	Published - 4 Jan 2016

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title = "A Second-Generation Chemoenzymatic Total Synthesis of Platencin",

abstract = "A total synthesis of the potent antibacterial agent platencin is described. The reaction sequence used involves, as starting material, an enantiomerically pure cis-1,2-dihydrocatechol derived from the whole-cell biotransformation of iodobenzene. Simple chemical manipulations of this metabolite provide a triene that engages in a thermally promoted intramolecular Diels–Alder reaction to establish the octahydro-2H-2,4a-ethanonaphthalene core of platencin.",

keywords = "Auger, electron current, photocurrent, radiation detection, self-powered, thin-film",

author = "{Rehmani N.}, Muhammad and {Alistair G.}, Draffan and {Martin G.}, Banwell and {Anthony C.}, Willis",

year = "2016",

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doi = "10.1055/s-0035-1560814",

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AU - Rehmani N., Muhammad

AU - Alistair G., Draffan

AU - Martin G., Banwell

AU - Anthony C., Willis

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Y1 - 2016/1/4

N2 - A total synthesis of the potent antibacterial agent platencin is described. The reaction sequence used involves, as starting material, an enantiomerically pure cis-1,2-dihydrocatechol derived from the whole-cell biotransformation of iodobenzene. Simple chemical manipulations of this metabolite provide a triene that engages in a thermally promoted intramolecular Diels–Alder reaction to establish the octahydro-2H-2,4a-ethanonaphthalene core of platencin.

AB - A total synthesis of the potent antibacterial agent platencin is described. The reaction sequence used involves, as starting material, an enantiomerically pure cis-1,2-dihydrocatechol derived from the whole-cell biotransformation of iodobenzene. Simple chemical manipulations of this metabolite provide a triene that engages in a thermally promoted intramolecular Diels–Alder reaction to establish the octahydro-2H-2,4a-ethanonaphthalene core of platencin.

KW - Auger

KW - electron current

KW - photocurrent

KW - radiation detection

KW - self-powered

KW - thin-film

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JO - Synlett

JF - Synlett

IS - 1

M1 - st-2015-d0783-l

ER -

A Second-Generation Chemoenzymatic Total Synthesis of Platencin

Abstract

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