There is very little information about Anna, daughter of Ivan II Ivanovich. Since the date of her birth is unknown, it is impossible to say for certain who her mother was: the first wife of Ivan Ivanovich Theodosia, who died just a year after the wedding [7, p. 16], or the second wife Alexandra, unknown by origin [10, p. 92].
There are several references in the sources that Anna, the daughter of the Grand Prince of Vladimir, was married. Two references in the Rogozhsky chronicler and the Nikon chronicle indicate that Ivan Ivanovich gave his daughter "to Lithuania" for "the grandson of Gediminas" [II, p. 228; III, cl. 65]. The Genealogy of Volyn princes mentions that Dmitri Ivanovich Donskoy married his sister Anna to Prince Dmitri Mikhailovich Bobrok of Volyn [I, p. 22, no. 6; IV, No. 174/280, l. 78; V, p. 111-112; 1, p. 285-286; 2, p. 2]. It is very difficult to establish the exact date of marriage. R.G. Skrynnikov believed that the marriage was concluded after 1379 [8, p. 66–67]. A. V. Kuzmin [4, p. 767, n. 212], V.A. Kuchkin etc. call an earlier date - c. 1356 [5, p. 249; 6, p. 10].
Due to discrepancies in the evidence, the very origin of Anna's husband Dmitry Bobrok of Volynalso is controversal. S.M. Soloviev spoke about him without delving into the problem of the origin [9, p. 264, 268, 272, etc.] V.O. Klyuchevsky considered him the son of Lyubart Gediminovich [3, p. 539-540]. A. V. Ekzempliarsky put forward the version that Dmitri was the son of the Lithuanian prince Koriyotas Gediminovich, who received the name of Mikhail in baptism [11, p. 135]. It was supported by V.A. Kuchkin [5, p. 249; 6, p. 10]. This version explains why in some sources Dmitry bears the patronymic "Mikhailovich". However, A. V. Kuzmin refuted the opinion that Dmitry Mikhailovich and Dmitry Koriatovich, mentioned in sources as Anna Ivanovna's husband, are the same person [4, p. 724-725]. To date, the question of the origin of Dmitry Bobrok of Volyn, who took part in the Battle of Kulikovo under the command of his brother-in-law Dmitry Ivanovich Donskoy, remains open. It is known that he took an active part in the political events of Muscow Rus, including negotiations with the khans and Lithuanian princes, participation in the Battle of Kulikovo and the struggle for power.
For Dmitry Bobrok of Volyn marriage with Anna was the second. They had a son, Vasily, who died in his youth as a result of an accident [1, p. 285-286]. As suggested by V.L. Yanin, under the impression of what happened Dmitry and Anna took tonsure and left worldly life [12, p. 52–61]. This version contradicts the opinion that Dmitry Koriatovich and Dmitry Mikhailovich are the same person.
The further fate of Anna and the date of her death are unknown.
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