Issue 3, 2018

Stereospecific C–H activation as a key step for the asymmetric synthesis of various biologically active cyclopropanes

Abstract

A rapid and efficient synthesis of hoshinolactam, an enantiopure cyclopropane containing natural product, is described. This strategy is based on stereospecific C(sp3)–H activation via unprecedented olefination on the cyclopropane core. The use of a stereogenic and easily recyclable directing group (S)-2-(p-tolylsulfinyl)aniline (APS) which was originally developed by our group allows obtention of diastereomerically pure products in high yields. Optically pure cyclopropanes are subsequently converted into enantiomerically pure targeted natural products. Furthermore a closely related synthetic scenario is employed to build up precursors of grenadamide and cascarillic acid.

Graphical abstract: Stereospecific C–H activation as a key step for the asymmetric synthesis of various biologically active cyclopropanes

Supplementary files

Article information

Article type
Research Article
Submitted
18 8月 2017
Accepted
15 9月 2017
First published
19 9月 2017

Org. Chem. Front., 2018,5, 409-414

Stereospecific C–H activation as a key step for the asymmetric synthesis of various biologically active cyclopropanes

S. Jerhaoui, P. Poutrel, J.-P. Djukic, J. Wencel-Delord and F. Colobert, Org. Chem. Front., 2018, 5, 409 DOI: 10.1039/C7QO00737J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements