41038-35-1Relevant articles and documents
Trans-stilbene as a starting material for the synthesis of tamoxifen based on palladium-catalyzed cross-coupling reactions
Nunes, Carolina M.,Limberger, Jones,Poersch, Silvia,Seferin, Marcus,Monteiro, Adriano L.
, p. 2761 - 2765 (2009)
(Z)-Tamoxifen was synthesized from a simple olefin (trans-stilbene) in 5 steps and 40% overall yield (Z/E = 74:26). The phenyl substituted group (4-Me2NCH2CH2OC6H4) was attached by a bromination-dehydrobromination-Suzuki reaction sequence. Subsequently, the ethyl group was attached to the triarylated olefin by a bromination-Negishi reaction sequence. Both the Suzuki and Negishi cross-coupling processes are stereospecific, and the stereo-selectivity depends only on the bromination-dehydrobromination reactions. (Z)-Tamoxifen was also obtained from trans-stilbene in only 3 steps by using Heck reaction-bromination- Negishi reaction sequence in 57% overall yield (Z/E = 65:35). Georg Thieme Verlag Stuttgart.