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

Abstract

Two myo-inositol derivatives (4) and (5), required for the total synthesis of surugatoxin, prosurugatoxin, and neosurugatoxin, were prepared. Synthesis of (±)-2,3-0-cyclohexylidene-4,5-0-isopropylidene-l-0-methoxymethyl-myw-inositol (4) was achieved from (±)-l-0~benzoyl-2,3-0-cyclohexylidene-4,5-0-isopropylidene-my0-inositol (6) in 4 steps, and (-)-2,3-0~cyclohexylidene-l,4-di-0-methoxymethyl-5-0-[2',3',4'-tri-0-acetyl-/J-D-xylopyranosyl]-/ffp0-inositol (5) was synthesized from (±)-l-0-benzoyl-2,3-0-cyclohexylidene-5,6-0-isopropylidene-/wp0-inositol (12) in 7 steps. © 1989, The Pharmaceutical Society of Japan. All rights reserved.