Tetrahedron Letters p. 4289 - 4291 (2013)
Update date:2022-08-11
Topics:
Christov, Plamen P.
Hawkins, Edward K.
Kett, Nathan R.
Rizzo, Carmelo J.
We previously reported the synthesis of the 1,N2-deoxyguanosine adducts of 4-hydroxynonenal, an important product of lipid peroxidation, which involved the nucleophilic aromatic substitution reaction of O 6-protected-2-fluoroinosine with 4-amino-1,2,5-trihydroxydecanal followed by periodate oxidation of the vicinal diol.6 An improved synthesis of the amino triols has been developed. The syn and anti diastereomers of a key intermediate, 4-nitro-5-hydroxy-1-decene, were synthesized by a Henry reaction and separated; each diastereomer was further separated into individual enantiomers by chiral supercritical fluid chromatography. Of note, dihydroxylation of the terminal olefin under conventional conditions with catalytic OsO4 and a tertiary amine oxide as the stoichiometric oxidant led to scrambling of stereochemistry of the nitro group. The scrambling was not observed when t-butylhydroperoxide was used as the oxidant.
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Doi:10.1080/10826068.2015.1045611
(2016)Doi:10.1016/S0040-4020(01)97082-6
(1974)Doi:10.1007/s11746-000-0179-1
(2000)Doi:10.1021/tx980157t
(1998)Doi:10.1021/jo00072a042
(1993)Doi:10.1021/acs.orglett.9b03514
(2019)