Yandong Zhang

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Name: 张延东; Zhang, YanDong

Organization: Xiamen University , China

Department: Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology

Title: Associate Professor(PhD)

TOPICS

Organic Chemistry

Chemicals
References

Synthesis of β-prolinols via [3+2] cycloaddition and one-pot programmed reduction: Valuable building blocks for polyheterocycles

Co-reporter:Jundong Li, Na Lin, Lei Yu, Yandong Zhang

Tetrahedron Letters 2016 Volume 57(Issue 51) pp:5777-5780

Publication Date(Web):21 December 2016

DOI:10.1016/j.tetlet.2016.11.035

•Our chemistry provides an efficient approach to highly functionalized β-prolinols.•The method features a [3+2] cycloaddition and a programmed reduction.•The resulting β-prolinols are valuable building blocks for polyheterocycles.A novel two-step synthesis of multisubstituted β-prolinols has been developed, featuring a [3+2] cycloaddition of azomethine ylides and a programmed reduction triggered by the combination of borane and lithium aluminum hydride (LAH). β-Prolinols are shown to be valuable building blocks for polyheterocycles.

Protecting-Group-Free Total Synthesis of (−)-Jiadifenolide: Development of a [4 + 1] Annulation toward Multisubstituted Tetrahydrofurans

Co-reporter:Yang Shen, Linbin Li, Zhisheng Pan, Yinglu Wang, Jundong Li, Kuangyu Wang, Xiance Wang, Youyu Zhang, Tianhui Hu, and Yandong Zhang

Organic Letters 2015 Volume 17(Issue 21) pp:5480-5483

Publication Date(Web):October 28, 2015

DOI:10.1021/acs.orglett.5b02845

A concise, protecting-group-free total synthesis of (−)-jiadifenolide, a synthetically challenging seco-prezizaane sesquiterpene with potent neurotrophic activity, is reported. The convergent route features a SmI2/H2O-mediated stereoselective reductive cyclization, an unprecedented formal [4 + 1] annulative tetrahydrofuran-forming reaction and programmed redox manipulations. The newly developed annulation of β-hydroxy aldehydes or ketones with lithium trimethylsilyldiazomethane provides access to a diverse array of multisubstituted tetrahydrofurans. The synthetic jiadifenolide exhibited weak cytotoxicity against five human cancer cell lines.

The Cyano Group as a Traceless Activation Group for the Intermolecular [3+2] Cycloaddition of Azomethine Ylides: A Five-Step Synthesis of ()-Isoretronecanol

Co-reporter:Jundong Li;Huaibo Zhao;Xunjin Jiang;Xiance Wang;Haiming Hu;Lei Yu ;Dr. Yong Zhang

Angewandte Chemie International Edition 2015 Volume 54( Issue 21) pp:6306-6310

Publication Date(Web):

DOI:10.1002/anie.201500961

Abstract

The cyano group was used as a traceless activation group for the [3+2] cycloaddition of azomethine ylides in a two-step process, thereby providing a highly effective approach to 5-unsubstituted pyrrolidines. The transformation includes the silver acetate catalyzed intermolecular 1,3-dipolar cycloaddition of α-iminonitriles and an unprecedented sodium borohydride induced reductive decyanation reaction. A diverse array of substrates is amenable to this transformation. The methodology was further extended to a five-step total synthesis of the pyrrolizidine natural product isoretronecanol.

The Cyano Group as a Traceless Activation Group for the Intermolecular [3+2] Cycloaddition of Azomethine Ylides: A Five-Step Synthesis of ()-Isoretronecanol

Co-reporter:Jundong Li;Huaibo Zhao;Xunjin Jiang;Xiance Wang;Haiming Hu;Lei Yu ;Dr. Yong Zhang

Angewandte Chemie 2015 Volume 127( Issue 21) pp:6404-6408

Publication Date(Web):

DOI:10.1002/ange.201500961

Abstract

Total Synthesis of (+)-Fusarisetin A Driven by a One-Pot Four-Reaction Process

Co-reporter:Chenguang Liu; Zhixiong Zeng; Renzhi Chen; Xunjin Jiang; Yinglu Wang

Organic Letters () pp:

Publication Date(Web):January 26, 2016

DOI:10.1021/acs.orglett.6b00036

A concise, asymmetric total synthesis of (+)-fusarisetin A, a hybrid natural product, has been achieved. A one-pot four-reaction process efficiently delivered the tetracycle 2 which served as a key intermediate for the synthesis of the title natural product and its analogues through amino acid incorporation.