Synthesis and Biological Activity of 7,8,9-Trideoxy- and 7R Des-THP-Peloruside A was written by Wullschleger, Christoph W.;Gertsch, Juerg;Altmann, Karl-Heinz. And the article was included in Chemistry – A European Journal in 2013.Quality Control of ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) This article mentions the following:
The stereoselective syntheses of 7,8,9-trideoxypeloruside A I and a monocyclic peloruside A analog lacking the entire tetrahydropyran moiety II are described. The syntheses proceeded through the PMB-ether of an ω-hydroxy β-keto aldehyde as a common intermediate which was elaborated into a pair of diastereomeric 1,3-syn and -anti diols by stereoselective Duthaler-Hafner allylation and subsequent 1,3-syn or anti reduction One of these isomers was further converted into a tetrahydropyran derivative in a high-yielding Prins reaction, to provide the precursor for bicyclic analog I. Downstream steps for both syntheses included the substrate-controlled addition of a vinyl lithium intermediate to an aldehyde, thus connecting the peloruside side chain to C15 (C13) of the macrocyclic core structure in a fully stereoselective fashion. In the case of monocyclic II macrocyclization was based on ring-closing olefin metathesis, while bicyclic I was cyclized through Yamaguchi-type macrolactonization. The macrolactonization step was surprisingly difficult and was accompanied by extensive cyclic dimer formation. Peloruside A analogs I and II inhibited the proliferation of human cancer cell lines in vitro with micromolar and sub-micromolar IC50 values, resp. The higher potency of I highlights the importance of the bicyclic core structure of peloruside A for nM biol. activity. In the experiment, the researchers used many compounds, for example, ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) (cas: 93379-49-8Quality Control of ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol)).
((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol) (cas: 93379-49-8) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. 1,3-Benzodioxole can be synthesized from catechol with disubstituted halomethanes.Quality Control of ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol)
Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem