Synthesis of the Antibiotic LL‐Z1120—Contribution to an Understanding of the 1,4‐Dioxocine System

Altenbach, Hans‐Josef; Lex, Johann; Linkenheil, Dieter; Voss, Burkhard; Vogel, Emanuel

doi:10.1002/anie.198409661

Cited by 6 publications

(1 citation statement)

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“…These dioxides were synthesisied by a different route and their thermal equilibration with the corresponding 1,4dioxocins was also reported. [27][28][29][30][31][32] The thermal valence tautomerisation of the syn-toluene dioxides 8d S and 11e S (ca. 77 • C in CCl 4 ) to the corresponding 1,4dioxocins 14d and 15 was followed by 1 H-NMR spectroscopy.…”

Section: Resultsmentioning

confidence: 99%

syn-Benzene dioxides: chemoenzymatic synthesis from 2,3-cis-dihydrodiol derivatives of monosubstituted benzenes and their application in the synthesis of regioisomeric 1,2- and 3,4-cis-dihydrodiols and 1,4-dioxocins

et al. 2007

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cis-2,3-Dihydrodiol metabolites of monosubstituted halobenzenes and toluene have been used as synthetic precursors of the corresponding 3,4-cis-dihydrodiols. Enantiopure syn-benzene dioxide intermediates were reduced to the 3,4-cis-dihydrodiols and thermally racemised via the corresponding 1,4-dioxocins. The syn-benzene dioxide-1,4-dioxocin valence tautomeric equilibrium ratio was found to be dependent on the substituent position. The methodology has also been applied to the synthesis of both enantiomers of the 1,2-(ipso)- and 3,4-cis-dihydrodiols of toluene. This chemoenzymatic approach thus makes available, for the first time, all three possible cis-dihydrodiol regioisomers of a monosubstituted benzene.

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