General Approach for the Liquid-Phase Fragment Synthesis of Orthogonally Protected Naturally Occurring Polyamines and Applications Thereof

Show full item record



Permalink

http://hdl.handle.net/10138/320721

Citation

Kalantzi , S , Athanassopoulos , C , Ruonala , R , Helariutta , Y & Papaioannou , D 2019 , ' General Approach for the Liquid-Phase Fragment Synthesis of Orthogonally Protected Naturally Occurring Polyamines and Applications Thereof ' , Journal of Organic Chemistry , vol. 84 , no. 23 , pp. 15118-15130 . https://doi.org/10.1021/acs.joc.9b02066

Title: General Approach for the Liquid-Phase Fragment Synthesis of Orthogonally Protected Naturally Occurring Polyamines and Applications Thereof
Author: Kalantzi, Stefania; Athanassopoulos, Constantinos; Ruonala, Raili; Helariutta, Ykä; Papaioannou, Dionissios
Contributor organization: Institute of Biotechnology
Organismal and Evolutionary Biology Research Programme
Viikki Plant Science Centre (ViPS)
Yrjö Helariutta / Principal Investigator
Plant Biology
Helsinki Institute of Life Science HiLIFE
Date: 2019-10-28
Language: eng
Belongs to series: Journal of Organic Chemistry
ISSN: 0022-3263
DOI: https://doi.org/10.1021/acs.joc.9b02066
URI: http://hdl.handle.net/10138/320721
Abstract: Orthogonally protected polyamines (PAs) have been synthesized using α,ω-diamines and ω-aminoalcohols as N-Cx-N and N-Cy synthons, respectively, and the Mitsunobu reaction as the key reaction for the assembly of the PA skeleta. The Trt, Dde, and Phth groups have been employed for protecting the primary amino functions and the Ns group for activating the primary amino functions toward alkylation and secondary amino function protection. The approach has been readily extended to accommodate the total synthesis of the spider toxins Agel 416 and HO-416b, incorporating the 3-4-3-3 and the 3-3-3-4 PA skeleton, respectively.
Subject: 116 Chemical sciences
Peer reviewed: Yes
Rights: unspecified
Usage restriction: openAccess
Self-archived version: acceptedVersion


Files in this item

Total number of downloads: Loading...

Files Size Format View
Manus_OPPAs_D.Papaioannou_REV_Oct_16_2019_.pdf 905.8Kb PDF View/Open

This item appears in the following Collection(s)

Show full item record