863224-35-5Relevant academic research and scientific papers
Total synthesis of quercitols: (+)- allo -, (-)- proto -, (+)- talo -, (-)- gala -, (+)- gala -, neo -, and (-)- epi -quercitol
Aucktor, Johannes,Brückner, Reinhard
, p. 250 - 258 (2015)
The cyclohexenenones exo- and endo-2 were converted into the cyclohexenyl acetates exo- and endo-3 and exo- and endo-5 with a diastereoselectivity of >99:1 (2 steps). Ether cleavage with DDQ in CH2Cl2/H2O (20:1) and in situ ketal hydrolysis afforded the cyclohexenones 6 and 7 in up to 83% and 87% yield, respectively. Compound 6 was converted into (+)-allo- and (-)-proto-quercitol with a diastereoselectivity of 100:0 (4 steps). Moreover, 6 was carried on to (-)-talo-quercitol whereas 7 furnished the four remaining title quercitols (3-5 steps) including both enantiomers of gala-quercitol.
Epoxidation of protected (1,4,5)-cyclohex-2-ene-triols and their acid hydrolysis to synthesize quercitols from D-(-)-quinic acid
Shih, Tzenge-Lien,Lin, Ya-Ling
, p. 1809 - 1817 (2007/10/03)
Highly stereoselective epoxidations have been achieved in both cyclohexylidene acetal and butane 2,3-bisacetal (BBA) protection of (1,4,5)-cyclohex-2-ene-triols. These epoxy derivatives are all derived from D-(-)-quinic acid and can be used for the synthe
