Seven-Step Total Synthesis of Sporothriolide

Miku Kimura, Tomoyo Mohri, Masaru Enomoto, Yasuhiro Meguro, Yusuke Ogura, Shigefumi Kuwahara

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)12475-12479
Number of pages5
JournalJournal of Organic Chemistry
Volume86
Issue number17
DOIs
Publication statusPublished - 2021 Sep 3

ASJC Scopus subject areas

  • Organic Chemistry

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