Synthesis of acyclic and heterocyclic natural products utilizing cyclitols as novel chiral building blocks

Enantiospecific Total Synthesis of (−)-D-Noviose

“…The observed abnormal regioselectivity of the Baeyer-Villiger rearrangement of 6 ( 3 7) came unexpected to us since it appeared in conflict with well-known rules; but similar results have been reported very recently by Chida and Ogawa [9]. To achieve the desired normal regiochemistry, it was obviously necessary to choose different protecting groups for the vicinal cis-dihydroxy moiety of 3 which had to display a stronger electron-withdrawing effect.…”

Regioselective Protection and Deprotection of Inositol Hydroxyl Groups

“…However, this approach needs to be pursued more vigorously in research related to inositols. Investigations on the chemistry of inositols have also had implications in areas of chemistry such as natural product synthesis, 5k, asymmetric synthesis, reaction mechanisms, development of novel metal complexing agents, , supramolecular chemistry, liquid crystals, , and polymers . Hence, it appears that the potential of using inositol derivatives in different areas of chemistry is ever-expanding and could open up newer areas of research and applications.…”

myo-Inositol 1,3-acetals as early intermediates during the synthesis of cyclitol derivatives

“…23,24 myoInositol has also been utilized for the synthesis of several natural products and their analogs. [25][26][27][28] Regioselective protection of myo-inositol hydroxyl groups is an arduous task since all the hydroxyl groups are secondary and the reactivity differences between them are subtle. Hence, reaction of myo-inositol (or its partially protected derivatives) with most reagents leads to the formation of a mixture of products; formation of acetals 13-16 of myo-inositol is shown in Scheme 2 as an example.…”