Catalytic Asymmetric Total Synthesis and Stereochemical Revision of Leucinostatin A: A Modulator of Tumor–Stroma Interaction. Issue 49 (10th August 2017)

• Record Type: Journal Article
• Authors: Abe, Hikaru; Ouchi, Hitoshi; Sakashita, Chiharu; Kawada, Manabu; Watanabe, Takumi; Shibasaki, Masakatsu
• Is Part Of: Chemistry. Volume 23:Issue 49(2017)
• Page Start: 11792
• Page End: 11796
• Publication Date: 2017-08-10
• Subjects: asymmetric catalysis -- configuration determination -- natural products -- total synthesis -- tumor-stroma interaction; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201703239
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Total synthesis of leucinostatin A, a modulator of tumor‐stroma interactions, using asymmetric catalyses, a nitroaldol reaction, thioamide‐aldol reaction, Strecker‐type reaction, and alcoholysis of 3‐methylglutaric anhydride, is described. We demonstrated the applicability of the established catalytic asymmetric processes to the synthesis of molecules with a complex structure. Careful analysis of the NMR data, HPLC profiles, and biological activity revealed that the correct structure of leucinostatin A is the epimeric form of the reported structure; the secondary alcohol within the AHMOD residue has an R configuration. Abstract : Asymmetric catalysis : Total synthesis of leucinostatin A, a modulator of tumor‐stroma interaction was achieved by applying four catalytic asymmetric reactions. Analysis of NMR data, HPLC profiles, and biological activity revealed that the correct structure of leucinostatin A is the epimer of the reported structure.