Strategy estrone synthesis

The homology of the tricyclic products in Scheme 6 to the ABC-ring portion of the steroid nucleus is obvious. In fact, the facility with which these tricyclic materials can be constructed from simple building blocks provided the impetus for the development of an exceedingly efficient synthesis of the female sex hormone, estrone (1). This important biomolecule has stimulated the development of numerous synthetic strategies and these have been amply reviewed.16 The remainder of this chapter is devoted to the brilliant synthesis of racemic estrone by K. P. C. Vollhardt et al.i2 17... 

Pattenden reported a tandem cyclization approach for the synthesis of estrone in 2004. Later, they further demonstrated that this strategy could be used to generate the veratramine skeleton [26]. 

Based on the use of 4-methoxybenzocyclobutene-1-carboxylic acid, racemic homoestrone has been synthesised (ref. 124). A strategy based on boron annulation led not directly to estrone but to a synthesis of norpregnenolone which was then degraded by standard procedures to afford estradiol derivatives (ref. 125). 

Probably the synthetically most useful versions of cyclotrimerization have been developed in the /ntromolecular sense through the pioneering work of Vollhardt. Since this topic has been thoroughly reviewed (95], we point out here only that the most powerful cyclocouplings have been two-component (e.g., diyne + mono-yne) or single component (e.g., ene-diyne) ones. The former strategy is elegantly illustrated in the CpCo(CO)2-catalyzed synthesis of estrone (61) depicted in Scheme 4-29 [105]. 

An estrone sensor was developed in Gao R. et al., 2011 by using a semicovalent imprinting strategy, which employed a thermally reversible covalent bond at the surface of silica coated CNTs. The synthesis of the nanocomposites involves silica shell deposition on the surface of CNTs, MIPs functionalized onto the silica surface, and final extraction of estrone by thermal reaction and generation of the recognition site. Authors state that the core-shell CNTs MIPs nanocomposites develofjed in this work can also be applied as a selective coating for electrochemical or quartz crystal microbalance sensors to monitor for estrone residue in environmental water... 

Estrone is an estrogenic hormone. Tietze s group reported a very elegant method for the enantioseletive total synthesis of estrone (Scheme 7.2) [6]. The best part of the strategy is the generation of the steroid ring B through consecutive inter- and intramolecular Heck reactions. They discovered that the treatment of functionalized aromatic compound 5 and the enantiopure hydrindene derivative 6 with Pd(OAc)2 and PPhj in the presence of -Bu NOAc in a mixed DMF/MeCN/H O... 

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