Total Synthesis of 15-D2t- and 15-epi-15-E2t-Isoprostanes | Zendy

Yasmin Brinkmann | Zendy; Camille Oger | Zendy; Alexandre Guy | Zendy; Thierry Durand | Zendy; JeanMarie Galano | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Open Access

Total Synthesis of 15-D_2t- and 15-epi-15-E_2t-Isoprostanes

Author(s) -

Yasmin Brinkmann,

Camille Oger,

Alexandre Guy,

Thierry Durand,

JeanMarie Galano

Publication year - 2010

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo1000274

Subject(s) - enantiopure drug , ozonolysis , isoprostanes , diol , total synthesis , chemistry , stereochemistry , isoprostane , enzyme , organic chemistry , enantioselective synthesis , catalysis , lipid peroxidation , arachidonic acid

The first total synthesis of 15-D(2t)-isoprostane is described. (-)-(9S,15S)-15-D(2t)-IsoP 1 and (+)-(11R,15R)-15-epi-15-E(2t)-IsoP 2 have been obtained in 15 steps from orthogonally protected enantiopure bicycle 3. Key features include an easy introduction of the cis side chains via ozonolysis, a highly selective enzymatic chemical differentiation of a non-meso-1,5-diol, and the use of a common synthetic intermediate allowing a stereodivergent approach to the target molecules.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research