title: Total synthesis of sphingofungin F by orthoamide-type overman rearrangement of an unsaturated ester.
abstract: The total synthesis of sphingofungin F through the Overman rearrangement of an unsaturated ester, which is known to be an unsuitable substrate under standard conditions due to the competitive aza-Michael reaction, is described. The developed conditions enabled the ester to be compatible with the original Overman rearrangement, providing quick access to α,α-disubstituted amino acids by minimizing extra protecting group manipulations and redox reactions.
authors.affiliation: †Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Shun
authors.initials: S
authors.lastname: Tsuzaki
authors.affiliation: †Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Shunme
authors.initials: S
authors.lastname: Usui
authors.affiliation: †Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Hiroki
authors.initials: H
authors.lastname: Oishi
authors.affiliation: †Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Daichi
authors.initials: D
authors.lastname: Yasushima
authors.affiliation: †Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Takahiro
authors.initials: T
authors.lastname: Fukuyasu
authors.affiliation: ‡School of Medicine, Keio University, 4-1-1, Hiyoshi, Kohoku-ku, Yokohama 223-8521, Japan.
authors.forename: Takeshi
authors.initials: T
authors.lastname: Oishi
authors.affiliation: †Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Takaaki
authors.initials: T
authors.lastname: Sato
authors.affiliation: †Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Noritaka
authors.initials: N
authors.lastname: Chida