Issue 8, 2017

Stereoselective strategies for the construction of polysubstituted piperidinic compounds and their applications in natural products’ synthesis

Abstract

Nitrogen-encompassing bioactive molecules can be regarded as the most frequently cited moieties, occurring either as natural products or as synthetically constructed chemical entities. One such framework which is abundantly found in both natural and synthetic chemical structures is the piperidinic core. A functionalized piperidinic core, either in natural products or in pharmaceuticals, is one of those immensely prevalent moieties. The piperidine frame can be seen in innumerable drug entities and this can be attributed to various reasons like the spacing obtained by piperidine structural conformers during the drug–receptor interactions, and solubility enhancement, hence resulting in improved pharmacokinetics and, most importantly, making the drug architecture metabolically stable. Further tapering down, 2, 4 and 6 substituted piperidines in general and with chiral centres in specific have attracted a substantial amount of attention in the recent past. This can be attributed to their diverse biological activities like analgesic, antimicrobial, sedative, antiasthmatic etc. In this communication, we aim to sum up and review all the reported methods since 2009 for the construction of the polysubstituted piperidinic core. Each method cited herein is exemplified with the synthesis of a natural compound and particularly alkaloids.

Graphical abstract: Stereoselective strategies for the construction of polysubstituted piperidinic compounds and their applications in natural products’ synthesis

Article information

Article type
Review Article
Submitted
08 رجب 1438
Accepted
01 شعبان 1438
First published
09 شعبان 1438

Org. Chem. Front., 2017,4, 1655-1704

Stereoselective strategies for the construction of polysubstituted piperidinic compounds and their applications in natural products’ synthesis

N. Kandepedu, I. Abrunhosa-Thomas and Y. Troin, Org. Chem. Front., 2017, 4, 1655 DOI: 10.1039/C7QO00262A

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