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Modular Synthesis of Multi-substituted Cyclobutanones Enabled by Oxyallyl Cations

Chinese Journal of Chemistry 2024年第5期42卷 459-463页

作者： Meng Wang Zhonggui Wang Ping Lu Research Center for Molecular Recognition and Synthesis Department of ChemistryFudan University220 Handan LuShanghai200433 China Present address: Department of Cancer Biology Dana-Farber Cancer Institute Department of Biological Chemistry and Molecular Pharmacology Harvard Medical SchoolBostonMA 02115USA

Stereoselective synthesis of multi-substituted cyclobutanes with different substituents is still a daunting challenge in organic synthesis.We report here a practical and facile approach to synthesizing all-trans 2,3,4-trisubstituted cyclobutanones from readily available dichlorocyclobutanones.The substitution reaction proceeds smoothly via oxyallyl cation intermediates under mild basic conditions.Further transformation to the synthesis of 1,2,3,4-tetrasubstituted cyclobutanes was also explored.

关键词： Diastereoselectivity Modular synthesis Nucleophilic substitution Organohalides Oxyallyl cation Precision functionalization strained molecules 1,2,3,4-Tetrasubstituted cyclobutanes

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Facile Generation of strained Peptidyl Thiolactones from Hydrazides and Its Application in Assembling MUC-1 VNTR OIigomers

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Chinese Journal of Chemistry 2021年第9期39卷 2509-2516页

作者： Yuankun Dao Biao Wang Weidong Dong Jun Zhang Chao Zhong Zhili Zhang Suwei Dong State Key Laboratory of Natural and Biomimetic Drugs and Department of Chemical BiologySchool of Pharmaceutical SciencesPeking UniversityBeijing 100191China Institute of Systems Biomedicine School of Basic Medical SciencesPeking University Health Science CenterBeijing 100191China

An efficient method for the activation of C-terminal 4-mecaptoproline-or penicillamine-containing peptide hydrazides in ligation re-actions is reported herein.The corresp on ding peptide hydrazides can be readily prepared using solid-phase peptide synthesis,and subsequently activated by acetylacet one(acac)without exoge nous thiol additives.strained peptidyl thiolactones could be the possible reactive in termediates that drastically accelerate the reacti on rates at the sterically demandi ng proline and valine sites.This developed protocol allows for sequential peptide ligations in a one-pot manner,and expedites the assembly of mucin 1(MUC-1)variable number tandem repeat(VNTR)trimers in various glycosylated forms.

关键词： strained molecules Glycopeptides Synthetic methods Peptidyl thiolactones

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Dancing on Ropes-Enantioselective Functionalization of Preformed Four-Membered Carbocycles

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Chinese Journal of Chemistry 2022年第11期40卷 1346-1358,I0002页

作者： Jun Chen Qiang Zhou Huayi Fang Ping Lu Research Center for Molecular Recognition and Synthesis Department of ChemistryFudan University220 Handan LuShanghai 200433China School of Materials Science and Engineering Tianjin Key Lab for Rare Earth Materials and ApplicationsNankai University38 Tongyan RoadTianjin 300350China

Cyclobutane derivatives have been recognized as useful structural motifs in organic synthesis and drug design.With the revival of photochemistry,the enantioselective synthesis of cyclobutane derivatives using[2+2]-cycloadditions has garnered numerous attentions.On the other hand,enantioselec-tive functionalization of preformed four-membered carbocycles is emerging as an important complementary approach to access chiral cyclobutane de-rivatives with versatile structural patterns.Herein,we summarize recent advances in this field from 2012.To avoid undesired C—C bond cleavage driv-en by strain-releasing,it is crucial to choose compatible methods for enantioselective functionalization and meanwhile preserving intact four-membered ring skeleton.Guided by calculated hydrogenation enthalpies,which are used to evaluate the strain energy of indicated C—C bond,a clear picture of the developed methodologies on functionalization of four-membered carbocycles combining the strain energy and enhanced reactivity is presented.

关键词： Enantioselective functionalization strained molecules Density functional calculations Strain-releasing C-H activation

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