Gabosines L, N and O: New Carba-Sugars fromStreptomyces with DNA-Binding Properties

Zirconocene-mediated deoxygenative ring contractions of vinyl-substituted carbohydrates: An expedient route to enantiomerically pure, densely functionalized 4-to-8-membered carbocycles

“…4 3 An entirely comparable mechanistic analysis can be applied to 5-vinylpyranosides [3]. For 18, the stereochemical course that is followed projects all three protected hydroxyls in the manner defined by 19 …”

“…Carbohydrate recognition events have often been probed with polyhydroxylated carbocyclic mimetics consisting uniquely of five-and six-membered cyclitols [18,19]. More recently, attention has been accorded to eight-membered ring systems, where the endocyclic oxygen atom of a pyranoside ring is replaced by a triad of methylene groups [20][21][22][23][24][25][26][27][28][29][30][31][32].…”

Synthesis of Marine-Derived Carbasugar Pericosines

“…The antidiabetes drug voglibose also has a carbasugar moiety [14]. Figure 1 presents the chemical structures of well-known carbasugars, valiolamine, validamycin A, (þ)-valienamine, (þ)-validamine, COCT, (À)-KD16-U1 (gabosine C), gabosines, and (þ)-MK7607 [15][16][17][18][19][20][21][22]. As they are attractive synthetic target molecules because of their various biological activities, synthetic studies of carbasugars are extremely important for drug discovery, in particular cancerpreventing drugs, and research has recently been progressing worldwide .…”

A common strategy for the synthesis of (+)-gabosine N, (+)-gabosine O, and some carbapyranoses using a Nozaki–Hiyama–Kishi reaction and RCM

“…4 Gabosines exhibit a variety of biological activities such as antiprotozoal, DNA binding properties, and enzyme inhibition. 5 Fifteen different gabosines have been isolated which possess the trihydroxy methyl (hydroxymethyl) cyclohexenone or cyclohexanone skeleton in common ( Fig. 1).…”