Stille/Diels-Alder reaction sequences: diversity-oriented access to novel steroids.
[reaction: see text] An efficient, diversity-oriented approach to novel steroid analogues possessing a C-5beta configuration begins with the Stille cross-coupling of enantiomerically pure cycloalkenylstannane trans-2 and enol triflate 3. The resulting diene trans-4 engages in Diels-Alder cycloaddition reactions with a range of dienophiles to give, after removal of protecting groups, biologically interesting 6,7-disubstituted steroid analogues.
Sünnemann
Hans Wolf
HW
Institut für Organische und Biomolekulare Chemie and Institut für Anorganische Chemie der Georg-August-Universität, Tammannstrasse 2-4, 37077 Göttingen, Germany.
Hofmeister
Anja
A
Magull
Jörg
J
Banwell
Martin G
MG
de Meijere
Armin
A
D000466:Alkadienes / Q000737:chemistry; D003432:Cross-Linking Reagents / Q000737:chemistry; D003500:Cyclization; D003516:Cycloparaffins / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry; D008956:Models, Chemical; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013256:Steroids / Q000138:chemical synthesis*; D017971:Tin Compounds / Q000737:chemistry*
D000466:Alkadienes; D003432:Cross-Linking Reagents; D003516:Cycloparaffins; D008698:Mesylates; D009942:Organometallic Compounds; D013256:Steroids; D017971:Tin Compounds; C031525:stannane; C012077:trifluoromethanesulfonic acid