Synthesis of methyl epi-anhydroquinate utilizing [2,3]-sigmatropic rearrangement of iodosoalkene

Sho Inomata, Minoru Ueda, Takeshi Sugai, Mitsuru Shoji

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Sigmatropic rearrangement has been utilized for stereoselective syntheses of structurally complicated natural products because of its high stereoselectivity and reactivity. Quinic acid (1) and its epimer 2 are versatile building blocks for the preparation of various bioactive compounds. We report the synthesis of methyl epi-anhydroquinate 3 via the [2,3]-sigmatropic rearrangement of iodosoalkene.

Original languageEnglish
Pages (from-to)1273-1275
Number of pages3
JournalChemistry Letters
Volume42
Issue number10
DOIs
Publication statusPublished - 2013

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Quinic Acid
Stereoselectivity
Biological Products

ASJC Scopus subject areas

  • Chemistry(all)

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Synthesis of methyl epi-anhydroquinate utilizing [2,3]-sigmatropic rearrangement of iodosoalkene. / Inomata, Sho; Ueda, Minoru; Sugai, Takeshi; Shoji, Mitsuru.

In: Chemistry Letters, Vol. 42, No. 10, 2013, p. 1273-1275.

Research output: Contribution to journalArticle

Inomata, Sho ; Ueda, Minoru ; Sugai, Takeshi ; Shoji, Mitsuru. / Synthesis of methyl epi-anhydroquinate utilizing [2,3]-sigmatropic rearrangement of iodosoalkene. In: Chemistry Letters. 2013 ; Vol. 42, No. 10. pp. 1273-1275.
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