Symmetry-Driven Total Synthesis of Myrioneurinol.

Aquilina, Jake M; Smith, Myles W

Aquilina, Jake M; Smith, Myles W.

Afiliación

Aquilina JM; Department of Biochemistry, UT Southwestern Medical Center, 5323 Harry Hines Blvd., Dallas, Texas 75390, United States.
Smith MW; Department of Biochemistry, UT Southwestern Medical Center, 5323 Harry Hines Blvd., Dallas, Texas 75390, United States.

J Am Chem Soc ; 144(25): 11088-11093, 2022 06 29.

Article en En | MEDLINE | ID: mdl-35699935

RESUMEN

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 â¼1% yield from commercial materials.

Asunto(s)

Alcaloides; Compuestos Heterocíclicos de 4 o más Anillos; Alcaloides/química; Alquenos/química; Aminación; Compuestos Heterocíclicos de 4 o más Anillos/química; Estereoisomerismo

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Alcaloides / Compuestos Heterocíclicos de 4 o más Anillos Idioma: En Revista: J Am Chem Soc Año: 2022 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Estados Unidos

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