Synthesis of chiral hydroxylated cyclopentanones and cyclopentanes

Enantioselective Synthesis of a Hydroxymethyl-cis-1,3-cyclopentenediol Building Block

“…Literature examples of the asymmetric synthesis of this moiety are limited to substrate-controlled diastereoselective alkylation 4b or asymmetric oxidation of prochiral substrates. 9 To the best of our knowledge, the enantioselective synthesis of the cis -1,3-cyclopentanediol scaffold has not been accomplished through asymmetric alkylation. As such, in concert with our research program dedicated to the development and application of the palladium-catalyzed asymmetric allylic alkylation, 10 we developed an efficient and general route for the enantioselective synthesis of cis -1,3-cyclopentanediol building block 1 .…”

“…The utility of cis -1,3-cyclopentanediols which contain a tertiary alcohol is severely limited due to the challenges associated with the stereocontrolled formation of such chiral centers. Literature examples of the asymmetric synthesis of this moiety are limited to substrate-controlled diastereoselective alkylation or asymmetric oxidation of prochiral substrates . To the best of our knowledge, the enantioselective synthesis of the cis -1,3-cyclopentanediol scaffold has not been accomplished through asymmetric alkylation.…”

Probing Autoinducer-2 Based Quorum Sensing: The Biological Consequences of Molecules Unable To Traverse Equilibrium States

“…In spite of the diminutive size of DPD, the chemical synthesis of DPD and its analogues has been a challenging issue because of their highly oxygenated frameworks, lability, and volatility. − Our target molecules have been no exception; indeed, there has been only one report of the synthesis of cis -DHMP and TriHMP that began from the asymmetric oxidation of 2-hydroxy-3-methylcyclopent-2-enone . Thus, we attempted to prepare cis -DHMP according to this route; however, we were not able to replicate the reported procedure due to significantly low yields, and only a trace amount of the desired product was obtained at the final step.…”

“…27-32 Our target molecules have been no exception; indeed, there has been only one report of the synthesis of cis -DHMP and TriHMP that began from the asymmetric oxidation of 2-hydroxy-3-methylcyclopent-2-enone. 33 Thus, we attempted to prepare cis -DHMP according to this route; however, we were not able to replicate the reported procedure due to significantly low yields, and only a trace amount of the desired product was obtained at the final step. As such, we were faced with the need to develop a more efficient synthesis of racemic cis -DHMP, shown in Scheme 1a.…”

“…This instability and degradation during silica gel column chromatography of cis -DHMP 5 were also described previously. 33 …”