Boyd, Derek R. , Sharma, Narain D. , MOREJÓN LLAMAS, NOEMÍ, O'Dowd, Colin R. , Allen, Christopher C. R.
Si
Org. Biomol. Chem.
Article
Científica
2.874
1.594
01/01/2006
000237907500014
Enantiopure cis-2,3-dihydrodiols, available from dioxygenase-catalysed cis-dihydroxylation of monosubstituted benzene substrates, have been used as synthetic precursors of the corresponding trans-3,4-dihydrodiols. The six-step chemoenzymatic route from cis-dihydrodiol precursors, involving acetonide, tetraol, dibromodiacetate and diepoxide intermediates, and substitution of vinyl bromide and iodide atoms, has been used in the synthesis of ten trans-dihydrododiol derivatives of substituted benzenes. The general applicability of the method has been demonstrated by its use in the synthesis of both enantiomers of the trans-1,2- and 3,4-dihydrodiol derivatives of toluene.