Synthesis of all possible regioisomers of scyllo-inositol phosphate

scyllo-Inositol is the all equatorial stereoisomer of myo-inositol. All pos sible 12 regioisomers of scyllo-inositol phosphate were synthesized for the first time via a scyllo-inositol benzoate intermediate, which was derived from a myo-inositol derivative. The stereoinversion of myo-inositol into sc yllo-inositol was accomplished by Mitsunobu reaction of the vicinal cis-dio l. The requisite intermediates, scyllo-inositol benzoates were obtained by benzoyl migration or random benzoylation, and phosphorylated to give scyllo -IPn. (C) 1999 Elsevier Science Ltd. All rights reserved.