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Synthetic Study of Kosinostatin Aglycon: Synthesis of the ABCDEFG Ring Skeleton
Yutaro Shimizu1, Shuhei Takahashi1, Takumi Iwata1
1Department of Applied Chemistry, Kyushu Institute of Technology, 1-1 Sensuicho, Tobata, Kitakyushu 804-8550, Japan.
Abstract:
A synthetic method for the CDEFG substructure of kosinostatin was developed using the cyclization of the di-para-nosyl 3-(2-hydroxyethyl)pyrrolidin-2-imine derivative. The key to the success of this cyclization was the choice of the para-nosyloxy (p-NsO) group as the leaving group. This selection enabled the cyclization to proceed under mild reaction conditions, leading to the first construction of a kosinostatin-type scaffold. The method was further applied to the synthesis of the ABCDEFG ring of kosinostatin aglycon.
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