Solid-phase synthesis of rigid acylpolyamines using temporary N-4,4'-dimethoxytrityl protection in the presence of trityl linkers

TY - JOUR

T1 - Solid-phase synthesis of rigid acylpolyamines using temporary N-4,4'-dimethoxytrityl protection in the presence of trityl linkers

AU - Olsen, Christian A

AU - Witt, Matthias

AU - Jaroszewski, Jerzy W

AU - Franzyk, Henrik

PY - 2004

Y1 - 2004

N2 - An N-protection protocol employing the 4,4'-dimethoxytrityl (Dmt) group in combination with borane reduction of resin-bound polyamides was shown to be an efficient methodology that enables synthesis of novel analogues of natural acylpolyamine toxins. Thus, three philanthotoxins containing polyamine chains with piperidyl and cyclohexyl structural elements, which introduce conformational rigidity, increased lipophilicity, and altered proteolytic properties, were obtained in 39-44% overall yield.

AB - An N-protection protocol employing the 4,4'-dimethoxytrityl (Dmt) group in combination with borane reduction of resin-bound polyamides was shown to be an efficient methodology that enables synthesis of novel analogues of natural acylpolyamine toxins. Thus, three philanthotoxins containing polyamine chains with piperidyl and cyclohexyl structural elements, which introduce conformational rigidity, increased lipophilicity, and altered proteolytic properties, were obtained in 39-44% overall yield.

KW - Boranes

KW - Catalysis

KW - Molecular Structure

KW - Polyamines

KW - Structure-Activity Relationship

KW - Trityl Compounds

KW - Wasp Venoms

U2 - 10.1021/jo049278q

DO - 10.1021/jo049278q

M3 - Journal article

C2 - 15373506

SN - 0022-3263

VL - 69

SP - 6149

EP - 6152

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 18

ER -