2006
DOI: 10.1002/ejoc.200600124
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Asymmetric Synthesis of Antithrombotic Agent M55529: The First Enantioselective Cyclic N,O‐Acetal Formation

Abstract: The first asymmetric synthesis of antithrombotic agent M55529 is reported, wherein the first enantioselective cyclic N,O-acetal formation is clarified.

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Cited by 8 publications
(9 citation statements)
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“…First, a salen-manganese complex, by which the cyclic N,O-acetal of M55529 was enantioselectively formed, [3] was examined for the formation of cyclic N,N-acetal 3 [Equa-tion (1)]. Desired cyclic N,N-acetal 3 was not obtained enantioselectively (0 % ee), but surprisingly, enantioenriched tricyclic compound 4 was instead obtained in 48 % ee.…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…First, a salen-manganese complex, by which the cyclic N,O-acetal of M55529 was enantioselectively formed, [3] was examined for the formation of cyclic N,N-acetal 3 [Equa-tion (1)]. Desired cyclic N,N-acetal 3 was not obtained enantioselectively (0 % ee), but surprisingly, enantioenriched tricyclic compound 4 was instead obtained in 48 % ee.…”
Section: Resultsmentioning
confidence: 99%
“…[2] We have also reported the enantioselective cyclic N,O-acetal formation and the asymmetric synthesis of M55529 with the use of a chiral salen-manganese complex (Scheme 1). [3] Scheme 1. Enantioselective cyclic N,O-acetal formation and the asymmetric synthesis of antithrombotic agent M55529.…”
Section: Introductionmentioning
confidence: 99%
“…[2] During the course of our development of an FXa inhibitor as an antithrombotic agent, we have reported the unique FXa inhibitor M55529, containing a cyclic N,O-acetal structure, [3] and an asymmetric synthesis of M55529 based on the enantioselective cyclic N,O-acetal formation using a chiral salen-manganese complex (Scheme 1). [4] Quite recently, we also reported other oral FXa inhibitors M58163 and M58169, [5] with characteristic features of a spiro unit and an imidazopyrazinone as a cyclic N,N-acetal structure instead of the cyclic N,Oacetal of M55529. These compounds exhibit higher FXa inhibitory activity [M58163 (IC 50 = 0.61 nM), M58169 (IC 50 = 0.58 nM)] than M55529 (IC 50 = 2.0 nM).…”
Section: Introductionmentioning
confidence: 93%
“…We report here the full account of the dynamic kinetic resolution in the amide formation step following formation of a cyclic N,N-acetal leading to the tricyclic key intermediate of M58163 and M58169 (Scheme 2). [10] Results and Discussion Enantioselective Cyclic N,N-Acetal Formation First, the chiral Brønsted acids and salen-manganese complex, by which the cyclic N,O-acetal had been obtained enantioselectively, [4] were examined. The results are summarized in Table 1.…”
Section: Introductionmentioning
confidence: 99%
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