Issue 14, 2018

Stereoselective preparation of key intermediates for the synthesis of iso-, neuro- and phyto-prostane family members: inaugural asymmetric synthesis of 17-E2c-dihomo- and 17-F2c-dihomo-isoprostanes

Abstract

A practical methodology for the synthesis of key intermediates for isoprostane, neuroprostane and dihomo-isoprostane preparation has been described. The key strategy involved a three stage C-12 stereocenter inversion of the configuration of a Corey lactone, commercially available in an enantiopure form. The key intermediate was then used to prepare 17-E2c-dihomo-isoprostane and 17-F2c-dihomo-isoprostane.

Graphical abstract: Stereoselective preparation of key intermediates for the synthesis of iso-, neuro- and phyto-prostane family members: inaugural asymmetric synthesis of 17-E2c-dihomo- and 17-F2c-dihomo-isoprostanes

Supplementary files

Article information

Article type
Communication
Submitted
26 fev 2018
Accepted
10 mar 2018
First published
13 mar 2018

Org. Biomol. Chem., 2018,16, 2393-2396

Stereoselective preparation of key intermediates for the synthesis of iso-, neuro- and phyto-prostane family members: inaugural asymmetric synthesis of 17-E2c-dihomo- and 17-F2c-dihomo-isoprostanes

A. Gandini, A. A. Amin, H. I. M. Amin, D. Corriero, A. Porta and G. Zanoni, Org. Biomol. Chem., 2018, 16, 2393 DOI: 10.1039/C8OB00489G

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