Total syntheses of shizukaols A and E

被引：35
|
作者：
Wu, Jian-Li [1 ,2 ]
Lu, Yin-Suo [1 ,2 ,3 ]
Tang, Bencan [4 ]
Peng, Xiao-Shui [1 ,2 ,5 ]
机构：
[1] Chinese Univ Hong Kong, Dept Chem, Shatin, Hong Kong, Peoples R China
[2] Chinese Univ Hong Kong, State Key Lab Synthet Chem, Shatin, Hong Kong, Peoples R China
[3] Shenzhen Salubris Pharmaceut Co LTD, Innovat Drug R&D Ctr, Shenzhen 518040, Peoples R China
[4] Univ Nottingham Ningbo China, Dept Chem & Environm Engn, Ningbo 315100, Zhejiang, Peoples R China
[5] Chinese Univ Hong Kong, Shenzhen Res Inst, Shenzhen Municipal Key Lab Chem Synth Med Organ M, Shenzhen 518507, Peoples R China
来源：
NATURE COMMUNICATIONS | 2018年 / 9卷
基金：
中国国家自然科学基金;
关键词：
SESQUITERPENOID DIMERS; CONCISE; KETONES; CHLORAHOLOLIDES; OLEFINATION; FRAMEWORK; BLOCKERS; POTENT; PLANTS; CORE;
D O I：
10.1038/s41467-018-06245-7
中图分类号：
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号：
07 ; 0710 ; 09 ;
摘要：
Shizukaols possess a common heptacyclic framework containing more than ten contiguous stereocenters and potential biological activities. Here we report that the total syntheses of shizukaols A (1) and E (2), two lindenane-type dimers from the Chloranthaceae family, are achieved via a modified biomimetic Diels-Alder reaction. The common crucial biomimetic diene 23 and ethylene species (6, 17) are obtained through either a highly Z-selective olefination of alpha-siloxy ketone with ynolate anions or an intramolecular Horner-Wadsworth-Emmons olefination from commercially available Wieland-Miescher ketone (7). This synthetic approach here opens up practical avenues for the total syntheses of the intriguing Chloranthaceae family members, as well as the understanding of their relevant biological action in nature.
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页数：7
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