title: A Total Synthesis of Bifidenone.
abstract: The first total synthesis of bifidenone, a novel natural tubulin polymerization inhibitor, has been achieved in 12 steps starting from commercially available 1,4-dioxaspiro[4.5]decan-8-one. The synthesis includes a newly developed method to generate the dihydrobenzodioxolone core by palladium-catalyzed aerobic dehydrogenation. The three stereocenters were installed with an AD-mix-β dihydroxylation step followed by a late-stage palladium-catalyzed decarboxylation-allylation procedure. The absolute stereochemistry of 3 was determined via 13a by single-crystal X-ray analysis.
authors.affiliation: Albany Molecular Research Inc., 1001 Main Street, Buffalo, New York 14203, United States.
authors.forename: Zhongping
authors.identifier: 0000-0001-8408-7243
authors.initials: Z
authors.lastname: Huang
authors.affiliation: Sequoia Sciences, Inc., 1912 Innerbelt Business Center Drive, St. Louis, Missouri 63114, United States.
authors.forename: Russell B
authors.identifier: 0000-0003-4534-3173
authors.initials: RB
authors.lastname: Williams
authors.affiliation: Sequoia Sciences, Inc., 1912 Innerbelt Business Center Drive, St. Louis, Missouri 63114, United States.
authors.forename: Mark
authors.initials: M
authors.lastname: O'Neil-Johnson
authors.affiliation: Sequoia Sciences, Inc., 1912 Innerbelt Business Center Drive, St. Louis, Missouri 63114, United States.
authors.forename: Gary R
authors.initials: GR
authors.lastname: Eldridge
authors.affiliation: Albany Molecular Research Inc., 1001 Main Street, Buffalo, New York 14203, United States.
authors.forename: John E
authors.initials: JE
authors.lastname: Mangette
authors.affiliation: Sequoia Sciences, Inc., 1912 Innerbelt Business Center Drive, St. Louis, Missouri 63114, United States.
authors.forename: Courtney M
authors.initials: CM
authors.lastname: Starks