
TY  - JOUR
A1  - Banwell, Martin G. 
A1  - Edwards, Alison J. 
A1  - McLeod, Malcolm D. 
A1  - Stewart, Scott G. 
T1  - A Chemoenzymatic Synthesis of the <emph type="2">cis</emph>-Decalin Core Associated with the Novel Anti-Mitotic Agent Phomopsidin: Some Observations Concerning a High-Pressure-Promoted Diels&ndash;Alder Cycloaddition Reaction of (1<emph type="2">S</emph>,2<emph type="2">R</emph>)-3-Methyl-<emph type="2">cis</emph>-1,2-dihydrocatechol and the Anionic Oxy&ndash;Cope Rearrangement of Compounds Derived from the Adduct
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 2004
VL  - 57
IS  - 7
SP  - 641
EP  - 644
KW  - 
UR  - https://doi.org/10.1071/CH04036 
N2  - The enantiomerically pure and enzymatically derived cis-1,2-dihydrocatechol 2 engages in a diastereofacially selective Diels&#8211;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&#x002F;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). Compound 16 also engages in an anionic oxy-Cope rearrangement reaction to give, depending on the molar equivalents of base used, either the cis-decalin 17 or the hexahydroindene 18. The structure of compound 18 has been established by single-crystal X-ray diffraction analysis. 
ER  -

