Toluene Dioxygenase-Mediated cis-Dihydroxylation of Aromatics in Enantioselective Synthesis. Asymmetric Total Syntheses of Pancratistatin and 7- …

…, K Königsberger, R Maurya, J Rouden…

Index: Hudlicky, Tomas; Tian, Xinrong; Koenigsberger, Kurt; Maurya, Rakesh; Rouden, Jacques; Fan, Boreas Journal of the American Chemical Society, 1996 , vol. 118, # 44 p. 10752 - 10765

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Citation Number: 161

Abstract

Whole-cell biooxidation of bromobenzene with Pseudomonas putida 39D or the recombinant Escherichia coli JM109 (pDTG601) yields (1 S, 2 S)-3-bromocyclohexa-3, 5- diene-1, 2-diol (9a), which is protected as the acetonide and converted to vinylaziridines 7, 15a, 63, and 64. Our route to (+)-pancratistatin features the coupling of a higher order cyanocuprate (derived by ortho-metalation from N, N-dimethyl-2-[(tert-butyldimethylsilyl) ...