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.
Department of Organic Chemistry and Research Group for Petrochemistry of the Hungarian Academy of Sciences, University of Veszprém, Veszprém, Hungary. skodane@almos.vein.hu
Rita
R
Skoda-Földes
Péter
P
Pfeiffer
Judit
J
Horváth
Zoltán
Z
Tuba
László
L
Kollár
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