Rapid mild macrocyclization of depsipeptides under continuous flow: total syntheses of five cyclodepsipeptides

Jingyuan Liao; Xuelei Jia; Fusong Wu; Junrong Huang; Guifu Shen; Hengzhi You; Fen Er Chen

doi:10.1039/d2qo01577c

Rapid mild macrocyclization of depsipeptides under continuous flow: total syntheses of five cyclodepsipeptides

Jingyuan Liao
, Xuelei Jia
, Fusong Wu
, Junrong Huang
, Guifu Shen
, Hengzhi You^*
, Fen Er Chen^*

^*Corresponding author for this work

Harbin Institute of Technology
Shenzhen Zhonghe Headway Bio-Sci & Tech Co.Ltd
Harbin Institute of Technology Shenzhen
Fudan University

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

The total synthesis of five natural products destruxin B, pseudodestruxin B, isaridin A, cladoamide A, and cladoamide B was accomplished. These depsipeptides were synthesized though a flow macrocyclization method from linear precursors, which were obtained by the solid-phase peptide synthesis (SPPS) method, and three different cyclization points (-CONHR, -CONR₂, -COOR) were designed to improve the total yield. In this study, the first examples of macrolactonization under flow were reported, and all 5 macrocyclizations were found to be significantly accelerated from hours to minutes. In addition, selective control of trans/cis conformers at the -CONR₂ cyclization point was revealed to be possible by employing suitable coupling reagents for macrolactamization.

Original language	English
Journal	Organic Chemistry Frontiers
Volume	23
Issue number	3
DOIs	https://doi.org/10.1039/d2qo01577c
State	Published - 20 Oct 2022
Externally published	Yes

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title = "Rapid mild macrocyclization of depsipeptides under continuous flow: total syntheses of five cyclodepsipeptides",

abstract = "The total synthesis of five natural products destruxin B, pseudodestruxin B, isaridin A, cladoamide A, and cladoamide B was accomplished. These depsipeptides were synthesized though a flow macrocyclization method from linear precursors, which were obtained by the solid-phase peptide synthesis (SPPS) method, and three different cyclization points (-CONHR, -CONR2, -COOR) were designed to improve the total yield. In this study, the first examples of macrolactonization under flow were reported, and all 5 macrocyclizations were found to be significantly accelerated from hours to minutes. In addition, selective control of trans/cis conformers at the -CONR2 cyclization point was revealed to be possible by employing suitable coupling reagents for macrolactamization.",

author = "Jingyuan Liao and Xuelei Jia and Fusong Wu and Junrong Huang and Guifu Shen and Hengzhi You and Chen, \{Fen Er\}",

note = "Publisher Copyright: {\textcopyright} 2022 The Royal Society of Chemistry.",

year = "2022",

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day = "20",

doi = "10.1039/d2qo01577c",

language = "英语",

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TY - JOUR

T1 - Rapid mild macrocyclization of depsipeptides under continuous flow

T2 - total syntheses of five cyclodepsipeptides

AU - Liao, Jingyuan

AU - Jia, Xuelei

AU - Wu, Fusong

AU - Huang, Junrong

AU - Shen, Guifu

AU - You, Hengzhi

AU - Chen, Fen Er

PY - 2022/10/20

Y1 - 2022/10/20

N2 - The total synthesis of five natural products destruxin B, pseudodestruxin B, isaridin A, cladoamide A, and cladoamide B was accomplished. These depsipeptides were synthesized though a flow macrocyclization method from linear precursors, which were obtained by the solid-phase peptide synthesis (SPPS) method, and three different cyclization points (-CONHR, -CONR2, -COOR) were designed to improve the total yield. In this study, the first examples of macrolactonization under flow were reported, and all 5 macrocyclizations were found to be significantly accelerated from hours to minutes. In addition, selective control of trans/cis conformers at the -CONR2 cyclization point was revealed to be possible by employing suitable coupling reagents for macrolactamization.

AB - The total synthesis of five natural products destruxin B, pseudodestruxin B, isaridin A, cladoamide A, and cladoamide B was accomplished. These depsipeptides were synthesized though a flow macrocyclization method from linear precursors, which were obtained by the solid-phase peptide synthesis (SPPS) method, and three different cyclization points (-CONHR, -CONR2, -COOR) were designed to improve the total yield. In this study, the first examples of macrolactonization under flow were reported, and all 5 macrocyclizations were found to be significantly accelerated from hours to minutes. In addition, selective control of trans/cis conformers at the -CONR2 cyclization point was revealed to be possible by employing suitable coupling reagents for macrolactamization.

UR - https://www.scopus.com/pages/publications/85141536099

U2 - 10.1039/d2qo01577c

DO - 10.1039/d2qo01577c

M3 - 文章

AN - SCOPUS:85141536099

SN - 2052-4110

VL - 23

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 3

ER -

Rapid mild macrocyclization of depsipeptides under continuous flow: total syntheses of five cyclodepsipeptides

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