Literature DB >> 30230670

Total Syntheses of Bisdehydroneostemoninine and Bisdehydrostemoninine by Catalytic Carbonylative Spirolactonization.

Kaiqing Ma1,2, Xianglin Yin1, Mingji Dai1.   

Abstract

The first total syntheses of the stemona alkaloids bisdehydroneostemoninine and bisdehydrostemoninine in racemic forms have been achieved. The synthetic strategy features a novel palladium-catalyzed carbonylative spirolactonization of a hydroxycyclopropanol to rapidly construct the oxaspirolactone moiety. It also features a Lewis acid promoted tandem Friedel-Crafts cyclization and lactonization to form the 5-7-5 tricyclic core of the target stemona alkaloids.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkaloids; cyclizations; natural products; palladium; total synthesis

Mesh：

Substances：

Year:  2018        PMID： 30230670      PMCID： PMC6459687          DOI： 10.1002/anie.201809114

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  36 in total

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2.  Cross metathesis of allyl alcohols: how to suppress and how to promote double bond isomerization.

Authors:  Bernd Schmidt; Sylvia Hauke
Journal:  Org Biomol Chem       Date:  2013-07-07       Impact factor: 3.876

3.  Enantioselective Total Synthesis of (+)-Neostenine.

Authors:  Yasuaki Nakayama; Yuichiro Maeda; Masayuki Kotatsu; Ruriko Sekiya; Masato Ichiki; Takaaki Sato; Noritaka Chida
Journal:  Chemistry       Date:  2016-02-02       Impact factor: 5.236

4.  Unified Total Synthesis of Stemoamide-Type Alkaloids by Chemoselective Assembly of Five-Membered Building Blocks.

Authors:  Makoto Yoritate; Yoshito Takahashi; Hayato Tajima; Chisato Ogihara; Takashi Yokoyama; Yasuki Soda; Takeshi Oishi; Takaaki Sato; Noritaka Chida
Journal:  J Am Chem Soc       Date:  2017-12-11       Impact factor: 15.419

5.  Synthesis and receptor profiling of Stemona alkaloid analogues reveal a potent class of sigma ligands.

Authors:  Kevin J Frankowski; Vincent Setola; Jon M Evans; Ben Neuenswander; Bryan L Roth; Jeffrey Aubé
Journal:  Proc Natl Acad Sci U S A       Date:  2011-02-28       Impact factor: 11.205

6.  Synthesis of the Common Core Structure of the Stemofoline Alkaloids.

Authors:  Eiji Ideue; Jun Shimokawa; Tohru Fukuyama
Journal:  Org Lett       Date:  2015-09-16       Impact factor: 6.005

7.  Total synthesis of (±)-maistemonine, (±)-stemonamide, and (±)-isomaistemonine.

Authors:  Zhi-Hua Chen; Zhi-Min Chen; Yong-Qiang Zhang; Yong-Qiang Tu; Fu-Min Zhang
Journal:  J Org Chem       Date:  2011-11-23       Impact factor: 4.354

8.  Synthesis of the stenine ring system from pyrrole.

Authors:  Roderick W Bates; S Sridhar
Journal:  J Org Chem       Date:  2011-05-16       Impact factor: 4.354

9.  Ruthenium-catalyzed cyclocarbonylation of allenyl alcohols and amines: selective synthesis of lactones and lactams.

Authors:  Eiji Yoneda; Shi-Wei Zhang; Da-Yang Zhou; Kiyotaka Onitsuka; Shigetoshi Takahashi
Journal:  J Org Chem       Date:  2003-10-31       Impact factor: 4.354

Review 10.  Structural relationships, distribution and biological activities of stemona alkaloids.

Authors:  Harald Greger
Journal:  Planta Med       Date:  2006-02       Impact factor: 3.352
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  8 in total

1.  Pyrrole Strategy for the γ-Lactam-Containing Stemona Alkaloids: (±)Stemoamide, (±)Tuberostemoamide, and (±)Sessilifoliamide A.

Authors:  Xianglin Yin; Kaiqing Ma; Ying Dong; Mingji Dai
Journal:  Org Lett       Date:  2020-06-17       Impact factor: 6.005

2.  Total Synthesis of trans-Resorcylide via Macrocyclic Stille Carbonylation.

Authors:  Yiyang Luo; Xianglin Yin; Mingji Dai
Journal:  J Antibiot (Tokyo)       Date:  2019-02-13       Impact factor: 2.649

3.  Total Synthesis, Biological Evaluation, and Target Identification of Rare Abies Sesquiterpenoids.

Authors:  Dexter C Davis; Dominic G Hoch; Li Wu; Daniel Abegg; Brandon S Martin; Zhong-Yin Zhang; Alexander Adibekian; Mingji Dai
Journal:  J Am Chem Soc       Date:  2018-12-06       Impact factor: 15.419

4.  Catalytic Hydroxycyclopropanol Ring-Opening Carbonylative Lactonization to Fused Bicyclic Lactones.

Authors:  Xinpei Cai; Weida Liang; Mingxin Liu; Xiating Li; Mingji Dai
Journal:  J Am Chem Soc       Date:  2020-07-27       Impact factor: 15.419

5.  Flow Chemistry-Enabled Divergent and Enantioselective Total Syntheses of Massarinolin A, Purpurolides B, D, E, 2,3-Deoxypurpurolide C, and Structural Revision of Massarinolin A.

Authors:  Ye-Cheng Wang; Chengsen Cui; Mingji Dai
Journal:  Angew Chem Int Ed Engl       Date:  2021-09-15       Impact factor: 15.336

Review 6.  Synthesis of Natural Products by C-H Functionalization of Heterocycless.

Authors:  Yang Zhang; Michal Szostak
Journal:  Chemistry       Date:  2022-02-17       Impact factor: 5.020

7.  Unique assembly of carbonylpyridinium and chromene reveals mitochondrial thiol starvation under ferroptosis and novel ferroptosis inducer.

Authors:  Kaiqing Ma; He Yang; Tianruo Shen; Yongkang Yue; Lingling Zhao; Xiaogang Liu; Fangjun Huo; Caixia Yin
Journal:  Chem Sci       Date:  2022-03-02       Impact factor: 9.825

8.  Cu-catalyzed hydroxycyclopropanol ring-opening cyclization to tetrahydrofurans and tetrahydropyrans: short total syntheses of hyperiones.

Authors:  Weida Liang; Xinpei Cai; Mingji Dai
Journal:  Chem Sci       Date:  2020-11-20       Impact factor: 9.825
  8 in total

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