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A short synthesis of ent‐hydromorphone has been achieved in twelve steps from β‐bromoethylbenzene. The key transformations involved the enzymatic dihydroxylation of the arene to the corresponding cis‐dihydrodiol, Mitsunobu coupling with the ring A fragment, oxidative dearomatization of the C3 phenol, and the subsequent [4+2] cycloaddition to form ring B of the morphinan. The synthesis was completed...
Eine 12‐stufige chemoenzymatische Totalsynthese führt T. Hudlicky und V. Varghese in ihrer Zuschrift auf S. 4444 ff. ausgehend von β‐Bromethylbenzol zu ent‐Hydromorphon. Schlüsselschritte sind eine enzymatische Dihydroxylierung, eine Mitsunobu‐Kupplung und eine oxidative Desaromatisierung mit anschließender intramolekularer [4+2]‐Cycloaddition. Nach den bahnbrechenden früheren Arbeiten zur Chemie...
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