Add time:07/25/2019         Source:sciencedirect.com

Publisher SummaryThe chapter discusses the synthesis of mannostatins, cyclophellitol and their analogues, focusing on the progress in the stereoselective, enantioselective and chiral synthesis. The structure of mannostatin A was first clarified to be (1,2,3,4/5)-4-amino-5-(methylthio)-l,2,3-cyclopentanetriol by nuclear magnetic resonance and mass spectrometry. This assignment and the absolute stereochemistry was later confirmed by X-ray crystallographic analysis of mannostatin B tetraacetate. Mannostatin B also contains a R configurational methylsulfinyl group. The high density and juxtaposition of functionality with the five chiral centers in the cyclopentane ring present an attractive synthetic target, and four independent syntheses, an improved synthesis, and two syntheses of analogues have been reported. A synthesis of (±)-mannostatin A and its positional isomer as the tetraacetyl derivative was first achieved from myo-inositol by Ogawa and Yuming. The meso (l,4,2,3,5/0)-5-acetamido-2,3-O-cyclohexylidene-l,4-di-O-mesylcyclopentane-l,2,3,4-tetraol prepared from (()-l,2-O-cyclohexylidene-myo-inositol) produced by the method proposed by Angyal et al, was converted into racemic (l,2,3,4,5/0)-5-acetamido-2,3-O-cyclohexylidenecyclopentane-l,2,3,4-tetraol by a procedure involving the configurational inversions at C-1 and C-4 via neighbouring-group participation of the 5-acetaniido group developed by Suami et al.

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