213599-26-9Relevant academic research and scientific papers
TOTAL SYNTHESIS OF ENANTIOPURE DESOGESTREL
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Page/Page column 25-26, (2009/04/25)
The present invention relates to a total synthesis of desogestrel and derivatives thereof, and to intermediate compounds of this synthesis.
Enantioselective total synthesis of the oral contraceptive desogestrel by a double heck reaction
Tietze, Lutz F.,Krimmelbein, Ilga K.
experimental part, p. 1541 - 1551 (2009/04/04)
A novel enantioselective total synthesis of the oral contraceptive desogestrel (2) is described, in which the tetracyclic steroid core is formed by a sequence of two consecutive Heck reactions. Conversion of the known enantiopure diketone 7 led to the chiral bicycle 6 which was used for a diastereoselective intermolecular Heck reaction with vinyliodide 5 to give 15. In the following intramolecular Heck reaction, the tetracyclic ring system was formed to give 4, from which the synthesis of desogestrel (2) was furnished.
Synthesis of novel spinosyn a analogues by Pd-mediated transformations
Tietze, Lutz F.,Brasche, Gordon,Grube, Alexander,Boehnke, Niels,Stadler, Christian
, p. 8543 - 8563 (2008/04/01)
The concept of modern crop protection demands for a continuous supply of new or modified established pesticides to avoid the development of serious resistances. Recent reports on the insecticidal spinosyns 1 and 2 show that also this class of pest managing agents is increasingly exposed to the formation of resistances. The synthesis of new derivatives is therefore highly desirable. We describe in this paper a convergent approach towards novel enantiopure spinosyn A analogues of type 3, which is based on investigations of structure-activity relationships and employs a twofold Heck reaction as key step for the preparation of the tricyclic backbone assembly.
Synthesis of enantiopure estrone via a double heck reaction
Tietze, Lutz F.,N?bel, Thomas,Spescha, Maurus
, p. 8971 - 8977 (2007/10/03)
A novel efficient catalytic approach to steroids by a double Heck reaction of the vinyl bromides 2 and the CD-building block 3 is presented. The new estrogen analogues 1a and 1b are formed via 23a and 23b in a highly regio- and stereoselective manner in g
