Synthesis Workshop: Synthesis of Anhydroryanodol (Episode 38) скачать в хорошем качестве

Synthesis Workshop: Synthesis of Anhydroryanodol (Episode 38)

In this Total Synthesis episode, we check out the Micalizio group's approach to anhydroryanodol. Parent reference: J. Am. Chem. Soc. 2020, 142, 12937-12941. Other references (in order of appearance): For isolation, see: (a) J. Am. Chem. Soc. 1948, 70, 3086-3088. (b) Phytochemistry 1993, 34, 397-400. For structural work, see: (a) Tetrahedron Lett. 1967, 8, 221-225. (b) Pure Appl. Chem. 1963, 7, 285-296. Prior syntheses in this family by Deslongchamps: Can J. Chem. 1979, 57, 3348-3354; Inoue: J. Am. Chem. Soc. 2014, 136, 5916-5919; Reisman: Science 2016, 353, 912-915. Prior work on this annulation from the Micalizio group: (a) J. Am. Chem. Soc. 2017, 139, 12374-12377. (b) Org. Lett. 2018, 20, 6457-6461. (c) Org. Lett. 2019, 21, 567-570. (d) Org. Lett. 2019, 21, 6126-6129. For more on this CuCl-mediated carbometallation reaction, see: Org. Biomol. Chem. 2009, 7, 3258-3263. For more on the Achmatowicz rearrangement, see: Tetrahedron 1971, 27, 1973-1996. For more on hydrogenation with Wilkinson’s catalyst [Rh(PPh3)3Cl], see: J. Chem. Soc. A 1966, 1711-1732. For more on the Stille coupling, see: J. Am. Chem. Soc. 1979, 101, 4992-4998. For more on this type of annulation, see: (a) J. Am. Chem. Soc. 2017, 139, 12374-12377. (b) Org. Lett. 2018, 20, 6457-6461. Reisman group’s approach to (+)-anhydroryanodol and (+)-ryanodol: Science 2016, 353, 912-915. For more on this Rh-catalyzed Pauson-Khand Reaction, see: Chem. Lett. 1998, 27, 249-250. For more on this ring-closing metathesis, see: J. Am. Chem. Soc. 2000, 122, 8168-8179. For the development of this radical epoxide reduction by the Gansäuer group, see: J. Am. Chem. Soc. 1998, 120, 12849-12859. Other recent application in Taxol synthesis (Baran group): J. Am. Chem. Soc. 2020, 142, 10526-10533.