Synthesis of novel structurally simplified estrogen analogues.
A library of 17 novel estrogen analogues 3 and 4 containing different substituents at rings A and D (steroid nomenclature) was prepared in a five- to seven-step synthesis. The key transformation is a Sonogashira-coupling of cyclic vinyl iodides of type 7 or 8 with phenylacetylenes of type 9. Reduction of the keto function in 3 led to the estradiol analogue 5.
Tietze
Lutz F
LF
Institut für Organische und Biomolekulare Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, Germany. ltietze@gwdg.de
Vock
Carsten A
CA
Krimmelbein
Ilga K
IK
Wiegand
J Matthias
JM
Nacke
Linda
L
Ramachandar
Tokala
T
Islam
Kazi M D
KM
Gatz
Christiane
C
D004958:Estradiol / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D004970:Estrone / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D054852:Small Molecule Libraries / Q000138:chemical synthesis*; D013237:Stereoisomerism
D054852:Small Molecule Libraries; D004970:Estrone; D004958:Estradiol