Asymmetric Total Synthesis of Nannocystin A

Abstract

Nannocystin A is a novel 21-membered macrolactone isolated from myxobacterium Nanocystis sp. It is a potent elongation factor 1 inhibitor and inhibits cancer cell line growth at nanomolar concentrations. In this work, a concise asymmetric total synthesis of nannocystin A has been developed, which features Sharpless epoxidation, Stille coupling, and final macrolactamization.

Design, Synthesis, and Photophysical Properties of Pyrroloquinoline‐Based Compounds Showing Strong Blue Fluorescence as Potential Dyes for Biomedical Applications

“…Samples were measured in a 10 mm quartz cell. For accurate measurement of the fluorescence, the concentration of the samples were in the range in which the Beer–Lambert law applies, and the optical density was <0.05 to avoid the inner filter effect . Emission spectra of all compounds were determined in the same medium as for absorption.…”

“…Due to their high sensitivity, rapid response time, and easy handling, fluorescent dyes are attractive and versatile labeling agents for a variety of analytical purposes, including cell culture studies and pharmacokinetic investigations . These labeling agents are usually classified into four groups according to their molecular structure: nucleic acids, peptides, polymers, and small molecules.…”

Negishi cross-couplings in the synthesis of amino acids

“…Usuki and co-workers utilised the same general strategy to build the Deomsine core as they had previously published. 78 A In 2017 the total synthesis of Nannocystin A 64 was reported by Liu et al 85 Within this report a Negishi cross-coupling of an iodo serine derviative was employed to build the key fragment 63 (Scheme 26). The final natural product was delivered with a longest linear sequence of 11 steps in a 5.3% overall yield.…”

“…Scheme 26 Total synthesis of nannocystin A, Liu et al 85 Scheme 27 Syn elimination of Boc protected amidozinc reagents.…”

Estudos visando a sí­ntese da caramboxina, uma toxina isolada de Averrhoa carambola

“…A síntese da "nannocystin A", molécula que mostrou relevantes resultados para a inibição do crescimento de células tumorais, reportada por Liu em 2017, faz uso do acoplamento de Negishi para a síntese de um derivado de fenilalanina importante para a rota sintética. O esquema 20 ilustra a síntese da nannocystin A (BRITTAIN e COBB, 2018;LIU et al, 2017).…”