Novel conformationally locked inositols: from aromatics to annulated cyclitols.
A new family of ring-annulated inositols with "locked" conformations has been designed to deliver a range of these biologically important entities in "unnatural conformations" while retaining their "natural configurations". The simple "tool" of trans ring fusion has been used to "lock" the conformation of the annulated inositols. Short, simple syntheses of a range of these novel cyclitols have been achieved from readily available aromatic precursors such as tetralin and indane. Along the way, annulated C(2)-symmetric cyclohexadiene-trans-diol (trans-CHD) derivatives have been prepared for the first time and serve as the pivotal building blocks for generating the oxy-functionalization pattern of inositols. The presence of chemo-differentiated hydroxyl groups in our novel inositols is expected to facilitate the installation of phosphate diversity to harness the biological potential of these entities.
Mehta
Goverdhan
G
Department of Organic Chemistry, Indian Institute Science Bangalore 560012 India. gm@orgchem.iisc.ernet.in
Senaiar
Ramesh S
RS
Bera
Mrinal K
MK
D007189:Indans / Q000737:chemistry; D007294:Inositol / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism; D013764:Tetrahydronaphthalenes / Q000737:chemistry
D007189:Indans; D013764:Tetrahydronaphthalenes; D007294:Inositol