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A Chemoenzymatic Synthesis of the cis -Decalin Core Associated with the Novel Anti-Mitotic Agent Phomopsidin: Some Observations Concerning a High-Pressure-Promoted Diels-Alder Cycloaddition Reaction of (1 S ,2 R )-3-Methyl- cis -1,2-dihydrocatechol and the Anionic Oxy-Cope Rearrangement of Compounds Derived from the Adduct

Banwell, Martin; Edwards, Alison; McLeod, Malcolm; Stewart, Scott

Description

The enantiomerically pure and enzymatically derived cis-1,2-dihydrocatechol 2 engages in a diastereofacially selective Diels-Alder cycloaddition reaction with commercially available lactone 3 at 19 kbar to afford adduct 4, which is readily elaborated to the diene-ol 13. Treatment of this last compound with KH/18 [crown]-6 resulted in successive anionic oxy-Cope and 1,2-Wittig rearrangements to afford acyloin 14 embodying the cis-decalin core associated with the natural product phomopsidin (1)....[Show more]

CollectionsANU Research Publications
Date published: 2004
Type: Journal article
URI: http://hdl.handle.net/1885/78450
Source: Australian Journal of Chemistry
DOI: 10.1071/CH04036

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