213337-05-4Relevant academic research and scientific papers
Allylboronates from vinyl triflates and α-chloroboronates by reductive nickel catalysis
Qiao, Jin-Bao,Zhao, Zhen-Zhen,Zhang, Ya-Qian,Yin, Kai,Tian, Zhi-Xiong,Shu, Xing-Zhong
, p. 5085 - 5089 (2020)
Allylboronates are unique building blocks widely used in organic synthesis, but the construction of cyclic allylboranates remains a challenging subject. We demonstrate here a mild and efficient access to this type of compound through the cross-electrophile coupling of vinyl triflates and α-chloroboronates. The reaction proceeded with a good substrate scope and good functional group compatibility. The ready availability of vinyl triflates from ketones, as well as the rich chemistry of allylboranates, makes our method suitable for the divergent modification of biologically active compounds. Preliminary mechanistic studies revealed that α-chloroboronates were activated via a radical process.
Design and synthesis of estrarubicin: A novel class of estrogen-anthracenedione hybrids
De Riccardis, Francesco,Meo, Daniela,Izzo, Irene,Di Filippo, Marcello,Casapullo, Agostino
, p. 1965 - 1970 (2007/10/03)
The synthesis of estrarubicin, a member of a new class of estrogen-anthraquinone hybrids, has been accomplished in an 8-step sequence starting from estrone. The octacyclic carbon skeleton has been elaborated by a Diels-Alder reaction using diene 5 and known epoxy-tetrone 6 as precursors. The cycloaddition reaction, performed in 5 M LiClO4 in diethyl ether, revealed notable diastereofacial selectivity of the diene, leading mainly to cycloadduct 8. Elaboration of the dihydroxyanthraquinone moiety and highly stereoselective epoxidation of the Δ17(20) bond yielded estrarubicin 2.
