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

Stefania Kalantzi | Zendy; Constantinos M. Athanassopoulos | Zendy; Raili Ruonala | Zendy; Ykä Helariutta | Zendy; Dionissios Papaioannou | Zendy

Open Access

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

Author(s) -

Stefania Kalantzi,

Constantinos M. Athanassopoulos,

Raili Ruonala,

Ykä Helariutta,

Dionissios Papaioannou

Publication year - 2019

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/acs.joc.9b02066

Subject(s) - chemistry , synthon , mitsunobu reaction , alkylation , primary (astronomy) , stereochemistry , protecting group , amino acid , combinatorial chemistry , solid phase synthesis , organic chemistry , biochemistry , peptide , alkyl , astronomy , catalysis , physics

Orthogonally protected polyamines (PAs) have been synthesized using α,ω-diamines and ω-aminoalcohols as N-C x -N and N-C y 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.

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