Convergent synthesis of tetrahydropyranyl side chain of verucopeptin, an antitumor antibiotic active against multidrug-resistant cancers

Yuanjun Sun; Wenhao Tang; Huxin Ni; Mei Wang; Bin Huang; Ya Qiu Long

doi:10.1039/d2cc04529j

Convergent synthesis of tetrahydropyranyl side chain of verucopeptin, an antitumor antibiotic active against multidrug-resistant cancers

Yuanjun Sun, Wenhao Tang, Huxin Ni, Mei Wang, Bin Huang, Ya Qiu Long^*

^*Corresponding author for this work

Soochow University

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

2 Citations (Scopus)

Abstract

A concise synthesis of the tetrahydropyranyl side chain of verucopeptin, an antitumor antibiotic cyclodepsipeptide efficacious against MDR cancers in vivo, is achieved using 12 steps in the longest linear sequence and 21 total steps, in which Julia-Kocienski olefination for the segments coupling, asymmetric hydroxylation as well as stereoselective synthesis of stable tetrahydropyran ring from a d-isoascorbic acid derivative are key steps. This convergent synthetic strategy enables the structural modification and mechanism study of verucopeptin for its clinical applications.

Original language	English
Pages (from-to)	13447-13450
Number of pages	4
Journal	Chemical Communications
Volume	58
Issue number	97
DOIs	https://doi.org/10.1039/d2cc04529j
Publication status	Published - 3 Nov 2022
Externally published	Yes

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Sun, Y., Tang, W., Ni, H., Wang, M., Huang, B., & Long, Y. Q. (2022). Convergent synthesis of tetrahydropyranyl side chain of verucopeptin, an antitumor antibiotic active against multidrug-resistant cancers. Chemical Communications, 58(97), 13447-13450. https://doi.org/10.1039/d2cc04529j

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abstract = "A concise synthesis of the tetrahydropyranyl side chain of verucopeptin, an antitumor antibiotic cyclodepsipeptide efficacious against MDR cancers in vivo, is achieved using 12 steps in the longest linear sequence and 21 total steps, in which Julia-Kocienski olefination for the segments coupling, asymmetric hydroxylation as well as stereoselective synthesis of stable tetrahydropyran ring from a d-isoascorbic acid derivative are key steps. This convergent synthetic strategy enables the structural modification and mechanism study of verucopeptin for its clinical applications.",

author = "Yuanjun Sun and Wenhao Tang and Huxin Ni and Mei Wang and Bin Huang and Long, {Ya Qiu}",

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T1 - Convergent synthesis of tetrahydropyranyl side chain of verucopeptin, an antitumor antibiotic active against multidrug-resistant cancers

AU - Sun, Yuanjun

AU - Tang, Wenhao

AU - Ni, Huxin

AU - Wang, Mei

AU - Huang, Bin

AU - Long, Ya Qiu

PY - 2022/11/3

Y1 - 2022/11/3

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AB - A concise synthesis of the tetrahydropyranyl side chain of verucopeptin, an antitumor antibiotic cyclodepsipeptide efficacious against MDR cancers in vivo, is achieved using 12 steps in the longest linear sequence and 21 total steps, in which Julia-Kocienski olefination for the segments coupling, asymmetric hydroxylation as well as stereoselective synthesis of stable tetrahydropyran ring from a d-isoascorbic acid derivative are key steps. This convergent synthetic strategy enables the structural modification and mechanism study of verucopeptin for its clinical applications.

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M3 - Article

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SN - 1359-7345

VL - 58

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EP - 13450

JO - Chemical Communications

JF - Chemical Communications

IS - 97

ER -

Convergent synthesis of tetrahydropyranyl side chain of verucopeptin, an antitumor antibiotic active against multidrug-resistant cancers

Abstract

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