Total Syntheses of Stoloniferol B and Penicitol A, and Structural Revision of Fusaraisochromanone

Tatsuki Ohashi, Seijiro Hosokawa*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

The first total synthesis of stoloniferol B and penicitol A has been achieved. Stoloniferol B, which is the common structure of citrinin derivatives, has been constructed by a sequential elaboration that includes a stereoselective vinylogous Mukaiyama aldol reaction, a thermal esterification with methyl acetoacetate, an intramolecular Michael reaction, and a vinylogous Dieckmann cyclization. The enantiomer of the proposed structure of fusaraisochromanone and (S)-7-hydroxy-3-((R)-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran-1(3H)-one (the enantiomer of a natural stoloniferol derivative) also have been synthesized. The synthesis revised the structure of fusaraisochromanone to (S)-7-hydroxy-3-((R)-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran-1(3H)-one.

Original languageEnglish
Pages (from-to)3021-3024
Number of pages4
JournalOrganic Letters
Volume20
Issue number10
DOIs
Publication statusPublished - 2018 May 18

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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