Complex Polypropionates from a South China Sea Photosynthetic Mollusk: Isolation and Biomimetic Synthesis Highlighting Novel Rearrangements

doi:10.1002/anie.202003643

	Complex Polypropionates from a South China Sea Photosynthetic Mollusk: Isolation and Biomimetic Synthesis Highlighting Novel Rearrangements
	Wu, Qihao 1,3; Li, Song-Wei 3,5; Xu, Heng 3; Wang, Hong 1; Hu, Pei 3; Zhang, Hao 3; Luo, Cheng 2,3; Chen, Kai-Xian 2,3; Nay, Bastien 4; Guo, Yue-Wei 2,3
刊名	ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
	2020-05-20
页码	9
关键词	biomimetic synthesis biosynthetic rearrangements marine natural products polyketides Sacoglossan mollusk
ISSN号	1433-7851
DOI	10.1002/anie.202003643
通讯作者	Nay, Bastien(bastien.nay@polytechnique.edu) ; Guo, Yue-Wei(ywguo@simm.ac.cn) ; Li, Xu-Wen(xwli@simm.ac.cn)
英文摘要	Placobranchus ocellatus is well known to produce diverse and complex gamma-pyrone polypropionates. In this study, the chemical investigation of P. ocellatus from the South China Sea led to the discovery and identification of ocellatusones A-D, a series of racemic non-gamma-pyrone polyketides with novel skeletons, characterized by a bicyclo[3.2.1]octane (1, 2), a bicyclo[3.3.1]nonane (3) or a mesitylene-substituted dimethylfuran-3(2H)-one core (4). Extensive spectroscopic analysis, quantum chemical computation, chemical synthesis, and/or X-ray diffraction analysis were used to determine the structure and absolute configuration of the new compounds, including each enantiomer of racemic compounds 1-4 after chiral HPLC resolution. An array of new and diversity-generating rearrangements is proposed to explain the biosynthesis of these unusual compounds based on careful structural analysis and comparison with six known co-occurring gamma-pyrones (5-10). Furthermore, the successful biomimetic semisynthesis of ocellatusone A (1) confirmed the proposed rearrangement through an unprecedented acid induced cascade reaction.
资助项目	National Natural Science Foundation of China (NSFC)[81991521] ; National Natural Science Foundation of China (NSFC)[41676073] ; National Natural Science Foundation of China (NSFC)[81520108028] ; National Natural Science Foundation of China (NSFC)[21672230] ; NSFC/CNRS joint project[81811530284] ; National Key Research and Development Program of China[2018YFC0310903] ; Drug Innovation Major Project[2018ZX09711-001-001-009] ; SKLDR/SIMM Project[SIMM1903ZZ-04] ; Chinese Academy of Sciences[2016258] ; SA-SIBS Scholarship Program
WOS关键词	MOLECULAR NETWORKING ; CIRCULAR-DICHROISM ; NATURAL-PRODUCTS ; BIOSYNTHESIS ; PATHWAYS ; PYRONES ; METABOLITES ; CHEMISTRY ; REVISION ; 1ST
WOS研究方向	Chemistry
语种	英语
出版者	WILEY-V C H VERLAG GMBH
WOS记录号	WOS:000534072800001
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/280330]
专题	中国科学院上海药物研究所
通讯作者	Nay, Bastien; Guo, Yue-Wei; Li, Xu-Wen
作者单位	1.Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou 310014, Peoples R China 2.Pilot Natl Lab Marine Sci & Technol, Open Studio Druggabil Res Marine Nat Prod, 1 Wenhai Rd, Qingdao 266237, Peoples R China 3.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 555 Chong Zhi Rd,Zhangjiang Hitech Pk, Shanghai 201203, Peoples R China 4.Ecole Polytech, Inst Polytech Paris, CNRS, Lab Synth Organ,ENSTA, F-91128 Palaiseau, France 5.Nanjing Univ Chinese Med, 138 Xianlin Rd, Nanjing 210023, Peoples R China
推荐引用方式 GB/T 7714	Wu, Qihao,Li, Song-Wei,Xu, Heng,et al. Complex Polypropionates from a South China Sea Photosynthetic Mollusk: Isolation and Biomimetic Synthesis Highlighting Novel Rearrangements[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2020:9.
APA	Wu, Qihao.,Li, Song-Wei.,Xu, Heng.,Wang, Hong.,Hu, Pei.,...&Li, Xu-Wen.(2020).Complex Polypropionates from a South China Sea Photosynthetic Mollusk: Isolation and Biomimetic Synthesis Highlighting Novel Rearrangements.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,9.
MLA	Wu, Qihao,et al."Complex Polypropionates from a South China Sea Photosynthetic Mollusk: Isolation and Biomimetic Synthesis Highlighting Novel Rearrangements".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020):9.