Scalable Synthesis of (-)-Rasfonin Enabled by a Convergent Enantioselective α-Hydroxymethylation Strategy

Robert K. Boeckman, Justin M. Niziol, Kyle F. Biegasiewicz

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

A scalable synthesis of the potent antitumor agent, (-)-rasfonin, has been achieved. The synthetic strategy features a highly convergent approach based on a single protocol construction of both major fragments via catalytic enantioselective α-hydroxymethylation of simple aliphatic aldehydes. The route described has been successful in the generation of gram quantities of the natural product and serves as the first synthetic strategy to provide sufficient material to continue studies related to its mechanism of action and potential as a cancer therapeutic.

Original languageEnglish (US)
Pages (from-to)5062-5065
Number of pages4
JournalOrganic Letters
Volume20
Issue number16
DOIs
StatePublished - Aug 17 2018
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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