Concise synthesis of (R)-reticuline and (+)-salutaridine by combining early-stage organic synthesis and late-stage biocatalysis

Abstract

The efficient access to the morphinan scaffold remains a major challenge in both synthetic chemistry and biotechnology. Here, a biomimetic chemo-enzymatic strategy to synthesize the natural promorphinan intermediate (+)-salutaridine is...

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“…A chemoenzymatic approach has been used for the asymmetric synthesis of the benzylisoquinoline alkaloid, ( R )-reticuline 40 and its promorphinan product, (+)-salutaridine 41 . 31 Reduction of an iminium salt using 1,2-dehydroreticuline reductase ( Ps DRR) gave reticuline 40 in 92% yield and >99% ee, while the use of membrane-bound salutaridine synthase led to selective ortho – para phenol coupling to give (+)-salutaridine 41 on a preparative scale (Scheme 3). …”