Synthesis of myo-Inositol Derivatives Required for the Total Synthesis of Surugatoxin, Prosurugatoxin, and Neosurugatoxin

Kunisuke OKADA; Kiyomatsu HASHIZUME; Hideo TANINO; Hisae KAKOI; Shoji INOUE

doi:10.1248/cpb.37.791

Kunisuke OKADA, Kiyomatsu HASHIZUME, Hideo TANINO, Hisae KAKOI, Shoji INOUE

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Keywords: 1, 2, 3, 4, 5-penta-O-substituted myo-inositol derivative, 2, 3-O-cyclohexylidene-4, 5-O-isopropylidene-1-O-methox-ymethyl-myo-inositol, 2, 3-O-cyclohexylidene-1, 4-di-O-methoxymethyl-5-O-[2', 3', 4'-tri-O-acetyl-β-D-xylopyranosyl]-myo-inositol, surugatoxin, prosurugatoxin, neosurugatoxin

JOURNAL FREE ACCESS

1989 Volume 37 Issue 3 Pages 791-793

DOI https://doi.org/10.1248/cpb.37.791

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Abstract

Two myo-inositol derivatives (4) and (5), required for the total synthesis of surugatoxin, prosurugatoxin, and neosurugatoxin, were prepared. Synthesis of (±)-2, 3-O-cyclohexylidene-4, 5-O-isopropylidene-1-O-methoxymethyl-myo-inositol (4) was achieved from (±)-1-O-benzoyl-2, 3-O-cyclohexylidene-4, 5-O-isopropylidene-myo-inositol (6) in 4 steps, and (-)-2, 3-O-cyclohexylidene-1, 4-di-O-methoxymethyl-5-O-[2', 3', 4'-tri-O-acetyl-β-D-xylopyranosyl]-myo-inositol (5) was synthesized from (±)-1-O-benzoyl-2, 3-O-cyclohexylidene-5, 6-O-isopropylidene-myo-inositol (12) in 7 steps.

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