Synthesis of bi- and tricyclic analogues of myo-inositol 3,4,5,6- and 1,4,5,6-tetrakisphosphate with extended carbon backbone

Schnaars, Andrew; Schultz, Carsten

doi:10.1016/s0040-4020(00)01021-8

Cited by 12 publications

(1 citation statement)

References 9 publications

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“…Lastly, a hydrophobic appendage in the form of an alicyclic ring in 2 could profoundly modulate the cell membrane permeability and receptor recognition parameters of the inositol moiety. Interestingly, the ring annulation maneuver on inositols, which leads to 2 , can be expected to alter their reactivity and biological profile and has not been attempted before 3h. More importantly, the annulated inositols are destined to be locked in “unnatural conformations” while retaining their “natural configurations”.…”

Section: Introductionmentioning

confidence: 99%

Novel Conformationally Locked Inositols: From Aromatics to Annulated Cyclitols

Mehta

Senaiar

Bera

2003

Chemistry A European J

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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.

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Section: Introductionmentioning

confidence: 99%