Bioinspired Network Analysis Enabled Divergent Syntheses and Structure Revision of Pentacyclic Cytochalasans

doi:10.1002/anie.202102831

KIB OpenIR

	Bioinspired Network Analysis Enabled Divergent Syntheses and Structure Revision of Pentacyclic Cytochalasans
	Wu,Hai ; Ding,Yiming ; Hu,Kun; Long,Xianwen ; Qu,Chunlei ; Puno,Pema-Tenzin ; Deng,Jun
	2021
Source Publication	ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
ISSN	1433-7851
Volume	60 Issue:29 Pages:15963-15971
Abstract	We accomplished the divergent total syntheses of ten pentacyclic cytochalasans (aspergillin PZ, trichodermone, trichoderones, flavipesines, and flavichalasines) from a common precursor aspochalasin D and revised the structures of trichoderone B, spicochalasin A, flavichalasine C, aspergilluchalasin based on structure network analysis of the cytochalasans biosynthetic pathways and DFT calculations. The key steps of the syntheses include transannular alkene/epoxyalkene and carbonyl-ene cyclizations to establish the C/D ring of pentacyclic aspochalasans. Our bioinspired approach to these pentacyclic cytochalasans validate the proposed biosynthetic speculation from a chemical view and provide a platform for the synthesis of more than 400 valuable cytochalasans bearing different macrocycles and amino-acid residues.
Keyword	bioinspired network analysis biomimetic synthesis natural products pentacyclic cytochalasans structure elucidation DIELS-ALDER REACTION ISOINDOLONE NUCLEUS RING-SYSTEM MEROCYTOCHALASANS REASSIGNMENT DESATURATION GENERATION ALKALOIDS CARBONATE SKELETONS
DOI	10.1002/anie.202102831
WOS ID	WOS:000662299400001
Citation statistics
Document Type	期刊论文
Identifier	http://ir.kib.ac.cn/handle/151853/73360
Collection	中国科学院昆明植物研究所
Affiliation	1.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, 132 Lanhei Rd, Kunming 650201, Yunnan, Peoples R China 2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China 3.Nankai Univ, Coll Chem, State Key Lab, Tianjin 300071, Peoples R China 4.Nankai Univ, Coll Chem, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China
Recommended Citation GB/T 7714	Wu,Hai,Ding,Yiming,Hu,Kun,et al. Bioinspired Network Analysis Enabled Divergent Syntheses and Structure Revision of Pentacyclic Cytochalasans[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2021,60(29):15963-15971.
APA	Wu,Hai.,Ding,Yiming.,Hu,Kun.,Long,Xianwen.,Qu,Chunlei.,...&Deng,Jun.(2021).Bioinspired Network Analysis Enabled Divergent Syntheses and Structure Revision of Pentacyclic Cytochalasans.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,60(29),15963-15971.
MLA	Wu,Hai,et al."Bioinspired Network Analysis Enabled Divergent Syntheses and Structure Revision of Pentacyclic Cytochalasans".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 60.29(2021):15963-15971.

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