Catalytic Asymmetric Total Synthesis of Leucinostatin A. Issue 1 (27th October 2020)

• Record Type: Journal Article
• Authors: Watanabe, Takumi; Abe, Hikaru; Shibasaki, Masakatsu
• Is Part Of: Chemical record. Volume 21:Issue 1(2021)
• Page Start: 175
• Page End: 187
• Publication Date: 2020-10-27
• Subjects: Total synthesis -- Catalytic asymmetric reaction -- Tumor-stroma interaction -- Antitumor agent -- Structure-activity relationship; Chemistry -- Periodicals; 540
• DOI: 10.1002/tcr.202000108
• Languages: English
• ISSNs: 1527-8999

Abstract

Abstract: This review describes our efforts toward achieving catalytic asymmetric total synthesis of leucinostatin A, a compound that interferes with the tumor‐stroma interaction. The synthesis utilizes four catalytic asymmetric reactions, including direct‐type reactions exemplified by high atom‐economy, and three C−C bond forming reactions. Thorough analysis of the NMR data, HPLC profiles, and biologic activity led us to unambiguously revise the absolute configuration regarding the 6‐position of the AHMOD residue side chain from S (reported) to R . Other examples of previously reported important studies on the stereoselective synthesis of HyLeu and AHMOD are also described. Abstract : In this review, a catalytic asymmetric total synthesis of leucinostatin A, a naturally occurring modulator of tumor‐stroma interaction, is described. The synthesis utilizes four catalytic asymmetric reaction conditions developed in this laboratory.