Total Synthesis of Paecilomycin B.
Starting from the glucose-derived δ-lactone and the functionalized aryl bromide, the first total synthesis of naturally occurring paecilomycin B was achieved via functionalized aryl-β-C-glycoside synthesis using 2,4,6-triisopropylphenyllithium under Barbier-type reaction conditions and ring-closing metathesis as the key steps.
†Medicinal Chemistry Research Laboratories, Mitsubishi Tanabe Pharma Corporation, 1000 Kamoshida-cho, Aoba-ku, Yokohama 227-0033, Japan.|‡Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
Kiyomi
K
Ohba
‡Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
Masaya
M
Nakata
D005947:Glucose / Q000737:chemistry*; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry*; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D006842:Hydrocarbons, Brominated; D007783:Lactones; D047028:Macrocyclic Compounds; C000601938:paecilomycin B; D005947:Glucose