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Symmetry-Driven Total Synthesis of Myrioneurinol.

ABSTRACT: We report a total synthesis of the Myrioneuron alkaloid myrioneurinol enabled by the recognition of hidden symmetry within its polycyclic structure. Our approach traces myrioneurinol's complex framework back to a symmetrical diketone precursor, a double reductive amination of which forges its central piperidine unit. By employing an inexpensive chiral amine in this key desymmetrizing event, four stereocenters of the natural product including the core quaternary stereocenter are set in an absolute sense, providing the first asymmetric entry to this target. Other noteworthy strategic maneuvers include utilizing a bicyclic alkene as a latent cis-1,3-bis(hydroxymethyl) synthon and a topologically controlled alkene hydrogenation. Overall, our synthesis proceeds in 18 steps and ∼1% yield from commercial materials.

SUBMITTER: Aquilina JM

PROVIDER: S-EPMC9721121 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature

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Symmetry-Driven Total Synthesis of Myrioneurinol.

Aquilina Jake M JM Smith Myles W MW

Journal of the American Chemical Society 20220614 25

We report a total synthesis of the <i>Myrioneuron</i> alkaloid myrioneurinol enabled by the recognition of hidden symmetry within its polycyclic structure. Our approach traces myrioneurinol's complex framework back to a symmetrical diketone precursor, a double reductive amination of which forges its central piperidine unit. By employing an inexpensive chiral amine in this key desymmetrizing event, four stereocenters of the natural product including the core quaternary stereocenter are set in an ...[more]

PMID: 35699935

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Project description:This study aimed to characterize ipsilateral loading and return to weight-bearing symmetry (WBS) in patients undergoing total hip arthroplasty (THA) during activities of daily living (ADLs) using instrumented insoles. A prospective study in 25 THA patients was performed, which included controlled pre- and postoperative follow-ups in a single rehabilitation center of an orthopedic department. Ipsilateral loading and WBS of ADLs were measured with insoles in THA patients and in a healthy control group of 25 participants. Measurements in the THA group were performed at 4 different visits: a week pre-THA, within a week post-THA, 3-6 weeks post-THA, and 6-12 weeks post-THA, whereas the healthy control group was measured once. ADLs included standing comfortably, standing evenly, walking, and sit-to-stand-to-sit (StS) transitions. All ADLs were analyzed using discrete methods, and walking included a time-scale analysis to provide temporal insights in the ipsilateral loading and WBS waveforms. THA patients only improved beyond their pre-surgery levels while standing comfortably (ipsilateral loading and WBS, p < 0.05) and during StS transitions (WBS, p < 0.05). Nevertheless, patients improved upon their ipsilateral loading and WBS deficits observed within a week post-surgery across all investigated ADLs. Ipsilateral loading and WBS of THA patients were comparable to healthy participants at 6-12 weeks post-THA, except for ipsilateral loading during walking (p < 0.05) at the initial and terminal double-leg support period of the stance phase. Taken together, insole measurements allow for the quantification of ipsilateral loading and WBS deficits during ADLs, identifying differences between pre- and postoperative periods, and differentiating THA patients from healthy participants. However, post-THA measurements that lack pre-surgery assessments may not be sensitive to identifying patient-specific improvements in ipsilateral loading and WBS. Moreover, StS transitions and earlier follow-up time points should be considered an important clinical metric of biomechanical recovery after THA.

Dataset Information

Symmetry-Driven Total Synthesis of Myrioneurinol.

Publications

Symmetry-Driven Total Synthesis of Myrioneurinol.

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