Total synthesis of (±)-xanthocidin using FeCl3-mediated Nazarov reaction

Kentaro Yaji, Mitsuru Shindo

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

The total synthesis of the antibiotic, (±)-xanthocidin (1), is described. The FeCl3-promoted fast Nazarov reaction of the β-alkoxy divinyl ketone in the presence of t-BuOH provided the α-exo-methylene cyclopentenone, which is the core skeleton of this natural product. After methoxymethyl (MOM) esterification and protection of the reactive exo-methylene unit with a phenylseleno group, dihydroxylation, followed by oxidation, gave xanthocidin MOM ester. Finally, this ester was converted into (±)-xanthocidin (1) under mild conditions.

Original languageEnglish
Pages (from-to)9808-9813
Number of pages6
JournalTetrahedron
Volume66
Issue number52
DOIs
Publication statusPublished - Dec 24 2010

Fingerprint

Esters
Esterification
Biological Products
Ketones
Skeleton
Anti-Bacterial Agents
Oxidation
alkoxyl radical
cyclopentenone
1,3-butadiene

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Total synthesis of (±)-xanthocidin using FeCl3-mediated Nazarov reaction. / Yaji, Kentaro; Shindo, Mitsuru.

In: Tetrahedron, Vol. 66, No. 52, 24.12.2010, p. 9808-9813.

Research output: Contribution to journalArticle

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