Synthesis of (4S,55′)-4,5-Dihydroxy-4,5-O-isopropylidene-2-cyclopenten-1-one fromd-Ribose

Synthesis and Biological Activity of Natural Aminocyclopentitol Glycosidase Inhibitors: Mannostatins, Trehazolin, Allosamidins, and Their Analogues

“…Inspite of the fact that racemic mixtures are obtained, this strategy has been exploited in the synthesis of mannostatins, trehazolin, and numerous analogues (e.g., Sections II.B.2 and III.B.2). Another aldol-like reaction involves an intermediate enolate (or enol complex) generated from a ribonolactone-derived 5- exo -enol ether to give an enone, which has subsequently served in routes to mannostatin and trehalamine (e.g., Sections II.B.3, II.B.4, and III.B.4).…”

“…Knapp and collaborators 61 have disclosed the synthesis of the aminocyclopentitol 136 , a precursor of trehalamine ( 93 ), starting from d -ribonolactone (Scheme ). The lactone was transformed into the hydroxycyclopentene 131 in 6 steps (see Scheme , ref b). Condensation of p -methoxybenzyl isothiocyanate with alcohol 131 and treating the product with iodine yielded the oxazolidinone 132 .…”