From toluene to triquinanes: Formal total syntheses of the sesquiterpenoid natural products (-)-hypnophilin and (-)-coriolin

David J.Y.D. Bon; Martin G. Banwell; Jas S. Ward; Anthony C. Willis

doi:10.1016/j.tet.2012.11.069

From toluene to triquinanes: Formal total syntheses of the sesquiterpenoid natural products (-)-hypnophilin and (-)-coriolin

David J.Y.D. Bon, Martin G. Banwell^*, Jas S. Ward, Anthony C. Willis

^*Corresponding author for this work

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

22 Citations (Scopus)

Abstract

The enantiomerically pure cis-1,2-dihydrocatechol 6, which is readily obtained via the whole-cell biotransformation of toluene, has been converted into the linear triquinane 3 using a reaction sequence involving Diels-Alder cycloaddition and oxa-di-π-methane rearrangement reactions as key steps. Compound 3 is an advanced intermediate associated with several previously reported total syntheses of the sesquiterpenoid natural products (-)-hypnophilin (1) and (-)-coriolin (2). Related chemistry has provided the tetracyclic compound 5, another established precursor to (-)-coriolin (2).

Original language	English
Pages (from-to)	1363-1368
Number of pages	6
Journal	Tetrahedron
Volume	69
Issue number	4
DOIs	https://doi.org/10.1016/j.tet.2012.11.069
Publication status	Published - 28 Jan 2013

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10.1016/j.tet.2012.11.069

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title = "From toluene to triquinanes: Formal total syntheses of the sesquiterpenoid natural products (-)-hypnophilin and (-)-coriolin",

abstract = "The enantiomerically pure cis-1,2-dihydrocatechol 6, which is readily obtained via the whole-cell biotransformation of toluene, has been converted into the linear triquinane 3 using a reaction sequence involving Diels-Alder cycloaddition and oxa-di-π-methane rearrangement reactions as key steps. Compound 3 is an advanced intermediate associated with several previously reported total syntheses of the sesquiterpenoid natural products (-)-hypnophilin (1) and (-)-coriolin (2). Related chemistry has provided the tetracyclic compound 5, another established precursor to (-)-coriolin (2).",

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T2 - Formal total syntheses of the sesquiterpenoid natural products (-)-hypnophilin and (-)-coriolin

AU - Bon, David J.Y.D.

AU - Banwell, Martin G.

AU - Ward, Jas S.

AU - Willis, Anthony C.

PY - 2013/1/28

Y1 - 2013/1/28

N2 - The enantiomerically pure cis-1,2-dihydrocatechol 6, which is readily obtained via the whole-cell biotransformation of toluene, has been converted into the linear triquinane 3 using a reaction sequence involving Diels-Alder cycloaddition and oxa-di-π-methane rearrangement reactions as key steps. Compound 3 is an advanced intermediate associated with several previously reported total syntheses of the sesquiterpenoid natural products (-)-hypnophilin (1) and (-)-coriolin (2). Related chemistry has provided the tetracyclic compound 5, another established precursor to (-)-coriolin (2).

AB - The enantiomerically pure cis-1,2-dihydrocatechol 6, which is readily obtained via the whole-cell biotransformation of toluene, has been converted into the linear triquinane 3 using a reaction sequence involving Diels-Alder cycloaddition and oxa-di-π-methane rearrangement reactions as key steps. Compound 3 is an advanced intermediate associated with several previously reported total syntheses of the sesquiterpenoid natural products (-)-hypnophilin (1) and (-)-coriolin (2). Related chemistry has provided the tetracyclic compound 5, another established precursor to (-)-coriolin (2).

KW - (-)-Coriolin

KW - (-)-Hypnophilin

KW - Diels-Alder

KW - Oxa-di-π-methane rearrangement

KW - Sesquiterpenes

KW - Triquinanes

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DO - 10.1016/j.tet.2012.11.069

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JO - Tetrahedron

JF - Tetrahedron

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From toluene to triquinanes: Formal total syntheses of the sesquiterpenoid natural products (-)-hypnophilin and (-)-coriolin

Abstract

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