Total synthesis of hirsutellide A

Xu, Yungen; Chen, Ligong; Duan, Xuemin; Meng, Yi; Jiang, Liqin; Li, Meiling; Zhao, Guang-Le; Li, Yang

doi:10.1016/j.tetlet.2005.04.087

Cited by 16 publications

(19 citation statements)

References 3 publications

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“…Xu et al. (2005) reported the first total synthesis of hirsutellide A 171 (Figure 18) in solution‐phase in nine steps, excluding the preparation of the building blocks [73] . Hirsutellide A is an 18‐membered cyclodepsipeptide, which was isolated from the cell extract of Hisutella kobayasii BCC 1660 and exhibits antimycobacterial and antimalarial [22] activities.…”

Section: Chemical Synthesis Of Precursor Cyclodepsipeptidesmentioning

confidence: 99%

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An Overview of the Synthesis of Biologically Active Cyclodepsipeptides

et al. 2022

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Cyclodepsipeptide are a class of natural cyclic peptides that have a wide range of biological activities, hence the potential to be developed as new drug candidates. Cyclodpesipeptides comprise a backbone of amide bonds and at least one ester moiety, thus are complex and challenging to synthesis. Generally, cyclodepsipeptides are synthesised via solid‐phase peptide synthesis, solution‐phase or a combination of solid and solution‐phase. Currently, solid‐phase peptide synthesis is more in demand, but it also has several challenges in its application especially for the cyclodepsipeptide that contains N‐methylated residues, as well as solution‐phase peptide synthesis tends to have a longer reaction step. Therefore, the combination of solid and solution‐phase peptide synthesis is a better alternative. This review discusses the synthetic strategies for cyclodepsipeptides including the preparation of precursor and macrocyclization.

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Section: Chemical Synthesis Of Precursor Cyclodepsipeptidesmentioning

confidence: 99%

“…Subsequently, the amine TFA salt of 177 was coupled to the free acid residue 178 employing the BOP−Cl reagent yielding 77 % of the desired linear hirsutellide A 179 (Scheme 34). [73] …”

Section: Chemical Synthesis Of Precursor Cyclodepsipeptidesmentioning

confidence: 99%

An Overview of the Synthesis of Biologically Active Cyclodepsipeptides

et al. 2022

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“…Notably, some synthetic methods for activating seco-acid groups to facilitate the formation of active ester in macrolactonization are also applicable to macrolactamization. For instance, the total synthesis of hirsutellide A ( 15 ) was achieved following a key macrolactamization step of 14 involving the phosphorus activating reagent BOP-Cl and DIPEA in a highly diluted DMF solution (1.0 mM) (Scheme 5) [87].…”

Section: Chemical Methodologies For the Construction Of Macrocyclesmentioning

confidence: 99%

Macrocyclic Drugs and Synthetic Methodologies toward Macrocycles

2013

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Macrocyclic scaffolds are commonly found in bioactive natural products and pharmaceutical molecules. So far, a large number of macrocyclic natural products have been isolated and synthesized. The construction of macrocycles is generally considered as a crucial and challenging step in the synthesis of macrocyclic natural products. Over the last several decades, numerous efforts have been undertaken toward the synthesis of complex naturally occurring macrocycles and great progresses have been made to advance the field of total synthesis. The commonly used synthetic methodologies toward macrocyclization include macrolactonization, macrolactamization, transition metal-catalyzed cross coupling, ring-closing metathesis, and click reaction, among others. Selected recent examples of macrocyclic synthesis of natural products and druglike macrocycles with significant biological relevance are highlighted in each class. The primary goal of this review is to summarize currently used macrocyclic drugs, highlight the therapeutic potential of this underexplored drug class and outline the general synthetic methodologies for the synthesis of macrocycles.

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“…However no cytotoxic effects were found against Vero cells at 50 µg/mL . A conventional solution synthesis, using standard reagents for ester (DCC, ( N , N '-dicyclohexylcarbodiimide) and amide bond (HATU) formation was developed by Xu [64,65]. In fact, the macrocylization reaction turned out problematic.…”

Section: Cyclohexadepsipeptidesmentioning

confidence: 99%

Cyclodepsipeptides: A Rich Source of Biologically Active Compounds for Drug Research

Sivanathan

Scherkenbeck

2014

Molecules

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Abstract:Faced with the need to find new drugs for all kinds of diseases, science sees that Nature offers numerous classes of compounds showing an impressively high biological potential. Among those are the cyclodepsipeptides, hybrid structures composed of amino and hydroxy acids. In the past decades numerous cyclodepsipeptides have been isolated and their potential as drugs has been studied extensively. For several cyclodepsipeptides total syntheses both in solution and on solid-phase have been established, allowing the production of combinatorial libraries. In addition, the biosynthesis of specific cyclodepsipeptides has been elucidated and used for the chemoenzymatic preparation of nonnatural analogues. This review summarizes the recent literature on cyclic tetra-to decadepsipeptides, composed exclusively of α-amino-and α-hydroxy acids.

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Total synthesis of hirsutellide A

Cited by 16 publications

References 3 publications

An Overview of the Synthesis of Biologically Active Cyclodepsipeptides

An Overview of the Synthesis of Biologically Active Cyclodepsipeptides

Macrocyclic Drugs and Synthetic Methodologies toward Macrocycles

Cyclodepsipeptides: A Rich Source of Biologically Active Compounds for Drug Research

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