No abstract

The stereoselective total synthesis of (+)‐petromyroxol, isolated from the water conditioned with the larval sea lamprey has been accomplished by employing the cross‐metathesis, tandem Sharpless asymmetric dihydroxylation/SN2 cyclization, and regioselective ring opening of epoxide as the key steps.

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A modified synthetic route to BMS-978587 was developed featuring a chemoselective nitro reduction and a stereospecific Suzuki coupling as the key bond formation steps. A systematic evaluation of the reaction conditions led to the identification of a robust catalyst/ligand/base combination to reproducibly effect the Suzuki reaction on large scale. The modified route avoided several challenges with the original synthesis and furnished the API in high overall yield and purity without recourse to chromatography.