Synthesis of Natural Products Utilizing Ring Cleavage Reaction of myo-Inositol Derivatives.

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  • Chida Noritaka
    Department of Applied Chemistry, Faculty of Science and Technology, Keio University

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  • ｍｙｏ‐イノシトールの環開裂反応を利用した天然物合成
  • myo イノシトール ノ カンカイレツハンノウ オ リヨウ シタ テンネンブツ ゴウセイ

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Abstract

myol-Inositol, a cyclitol (cyclohexanepolyol) which is classified as a type of carbohydrates, occurs widely in nature and is known as a constituent of a secondary messenger in cells which stimulates the release of calcium from storage site. It is produced in large quantities from plants (rice bran and corn-steep liquors) by food industry. In spite of its abundance in nature and ready availability, myol-inositol has not been utilized widely as the starting material for the synthesis of natural products other than cyclitol derivatives. Given that regioselective ring cleavage of the cyclohexane ring in optically active and functionalized cyclitol derivatives is possible, myol-inositol is expected to be a potential precursor with stereochemical diversity for novel chiral building blocks in the synthesis of various natural products. In this article, preparation and optical resolution of protected myol-inositol derivatives are shortly reviewed. Overview of regioselective ring cleavages of cyclohexanones derived from cyclitols by way of the Baeyer-Villiger reaction, and the syntheses of some natural products based on the methodologies which involve the ring cleavage reaction of myol-inositol, is also described.

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