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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Seven-Step Total Synthesis of Sporothriolide
Miku Kimura1, Tomoyo Mohri1, Masaru Enomoto1
1Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University, 468-1 Aramaki-Aza-Aoba, Aoba-ku, Sendai 980-0845, Japan.
Abstract:
An enantioselective total synthesis of sporothriolide, a bioactive furofurandione-type fungal metabolite, has been achieved in a 21% overall yield from a commercially available β,γ-unsaturated carboxylic acid via seven steps. The key steps of this synthesis include a highly diastereoselective Michael addition of a chiral oxazolidinone derivative to a nitro olefin, the exploitation of an aromatic ring as a masked carboxylic acid functionality, and the base-promoted elimination of nitrous acid to install the α-methylene lactone unit of sporothriolide in the final step.
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