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

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. Com...

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Bibliographic Details
Published in:Tetrahedron 2013-01, Vol.69 (4), p.1363-1368
Main Authors: Bon, David J.-Y.D., Banwell, Martin G., Ward, Jas S., Willis, Anthony C.
Format: Article
Language:English
Subjects:
(−)-Coriolin
(−)-Hypnophilin
Diels–Alder
Oxa-di-π-methane rearrangement
Sesquiterpenes
Triquinanes
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Summary: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). [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2012.11.069