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

Sho Inomata; Minoru Ueda; Takeshi Sugai; Mitsuru Shoji

doi:10.1246/cl.130612

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

Sho Inomata, Minoru Ueda, Takeshi Sugai, Mitsuru Shoji

School of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

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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 language	English
Pages (from-to)	1273-1275
Number of pages	3
Journal	Chemistry Letters
Volume	42
Issue number	10
DOIs	https://doi.org/10.1246/cl.130612
Publication status	Published - 2013

ASJC Scopus subject areas

Chemistry(all)

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10.1246/cl.130612

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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.",

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PY - 2013

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AB - 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.

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

Abstract

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