Microwave-assisted Stille-coupling of steroidal substrates.
Steroidal dienes were synthesised by Stille-coupling of the corresponding alkenyl iodides with vinyltributyltin under microwave irradiation in a domestic microwave oven in drastically reduced reaction times. Rate acceleration was observed also in the one-pot Stille-coupling-Diels-Alder reaction of 17-iodo-5alpha-androst-16-ene. Stereoselectivity of cycloaddition was slightly improved with diethyl maleate as the dienophile, compared to that achieved with thermal heating.
Skoda-Földes
Rita
R
Department of Organic Chemistry and Research Group for Petrochemistry of the Hungarian Academy of Sciences, University of Veszprém, Veszprém, Hungary. skodane@almos.vein.hu
Pfeiffer
Péter
P
Horváth
Judit
J
Tuba
Zoltán
Z
Kollár
László
L
D000475:Alkenes / Q000737:chemistry* / Q000528:radiation effects; D006358:Hot Temperature; D007454:Iodides / Q000737:chemistry* / Q000528:radiation effects; D008298:Maleates / Q000737:chemistry; D008872:Microwaves; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013256:Steroids / Q000737:chemistry* / Q000528:radiation effects
D000475:Alkenes; D007454:Iodides; D008298:Maleates; D013256:Steroids; D010165:Palladium; C014476:diethyl maleate