582300-15-0Relevant articles and documents
A new approach toward the synthesis of C,D-cis coupled steroid and C,D-cis coupled D-homosteroid skeletons
Dratch, Svetlana,Charnikhova, Tanya,Sarabèr, Florence C.E.,Jansen, Ben J.M.,De Groot, Aede
, p. 4287 - 4295 (2003)
A short and efficient procedure has been developed for the synthesis of C,D-cis coupled steroid and D-homo steroid skeletons. A Mukaiyama reaction with transfer of the silyl group of the starting silyl enol ether to the enol of the adduct followed by addition of vinyl magnesium bromide to the unprotected carbonyl group leads to adducts which can be cyclized with ZnBr2. The synthesis of functionalized steroid skeletons in overall yields of about 50% in four steps can be achieved in this way.
Domino Mukaiyama-Michael reactions in the synthesis of polycyclic systems
Sarabèr, Florence C. E.,Dratch, Svetlana,Bosselaar, Geke,Jansen, Ben J. M.,De Groot, Aede
, p. 1717 - 1725 (2007/10/03)
Good results were obtained in the Mukaiyama-Michael reaction of the silyl enol ether of cyclohexanone with 2-methyl-2-cyclopentenone and carvone, with transfer of the silyl group to the receiving enone and with TrSbCl6 as catalyst. A second Mukaiyama-Michael reaction of this new silyl enol ether with methyl vinyl ketone and cyclization of the resulting adduct leads to tricyclic compounds in one-pot domino sequences. The scope and limitations of this domino reaction have been investigated.
