Simple circular dichroic method for the determination of absolute configuration of 5-substituted 2(5H)-furanones Gawronski, J.K.; van Oeveren, A.; van der Deen, H.; Leung, C.W; Feringa, B.L.

The development of a commercial manufacturing process for fulvestrant (the active ingredient in 'Faslodex') is described. Key steps in the synthesis are stereoselective 1,6-addition of an organocuprate to a steroidal dienone followed by copper-mediated aromatisation of the A-ring. The strategy for dealing with noncrystalline intermediates is outlined. The production of drug substance of acceptable quality is critically dependent on limiting the formation of key impurities. The origin of these impurities is discussed, and measures to prevent or control their formation are described.

Racemic 5-alkoxyfuran-2(5H)-ones and 5-methoxydihydrofuran-2(3H)-one are resolved by inclusion complexation employing a crystallization or suspension method with tartaric acid-derived chiral hosts.

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