129150-61-4Relevant articles and documents
Gram-scale enantioselective formal synthesis of morphine through an orth?para oxidative phenolic coupling strategy
Tissot, Matthieu,Phipps, Robert J.,Lucas, Catherine,Leon, Rafael M.,Pace, Robert D.M.,Ngouansavanh, Tifelle,Gaunt, Matthew J.
, p. 13498 - 13501 (2014)
A gram-scale catalytic enantioselective formal synthesis of morphine is described. The key steps of the synthesis involve an orth?para oxidative phenolic coupling and a highly diastereoselective "desymmetrization" of the resulting cyclohexadienone that generates three of the four morphinan ring junction stereocenters in one step. The stereochemistry is controlled from a single carbinol center installed through catalytic enantioselective hydrogenation. These transformations enabled the preparation of large quantities of key intermediates and could support a practical and scalable synthesis of morphine and related derivatives.
A new approach to combretastatin D2
Cousin, David,Mann, John,Nieuwenhuyzen, Mark,Van Den Berg, Hendrik
, p. 54 - 62 (2007/10/03)
A concise and convergent route to combretastatin D2 is described together with some preliminary biological data. The Royal Society of Chemistry 2006.
An Ullmann ether reaction involving an alkynyl substrate: A convergent route to a combretastatin intermediate
Blase,Banerjee
, p. 3187 - 3197 (2007/10/02)
We found that we could employ a disubstituted alkynyl halide in an Ullmann ether reaction to produce the cis-alkene intermediate 3 of the combretastatin natural products.