Literature DB >> 26181605

Asymmetric Total Synthesis of Propindilactone G.

Lin You1, Xin-Ting Liang1, Ling-Min Xu1, Yue-Fan Wang1, Jia-Jun Zhang1, Qi Su1, Yuan-He Li1, Bo Zhang1, Shou-Liang Yang1, Jia-Hua Chen1, Zhen Yang1,2,3.   

Abstract

A concise total synthesis of (+)-propindilactone G, a nortriterpenoid isolated from the stems of Schisandra propinqua var. propinqua, has been achieved for the first time. The key steps of the synthesis include an asymmetric Diels-Alder reaction, a Pauson-Khand reaction, a Pd-catalyzed reductive hydrogenolysis reaction, and an oxidative heterocoupling reaction. These reactions enabled the synthesis of (+)-propindilactone G in only 20 steps. As a consequence of our synthetic studies, the structure of (+)-propindilactone G has been revised.

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Year:  2015        PMID: 26181605     DOI: 10.1021/jacs.5b06480

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  12 in total

Review 1.  Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products.

Authors:  Zachary G Brill; Matthew L Condakes; Chi P Ting; Thomas J Maimone
Journal:  Chem Rev       Date:  2017-03-15       Impact factor: 60.622

2.  Recent Advances in the Pauson-Khand Reaction.

Authors:  J David Ricker; Laina M Geary
Journal:  Top Catal       Date:  2017-03-30       Impact factor: 2.910

Review 3.  Radicals: Reactive Intermediates with Translational Potential.

Authors:  Ming Yan; Julian C Lo; Jacob T Edwards; Phil S Baran
Journal:  J Am Chem Soc       Date:  2016-09-26       Impact factor: 15.419

4.  Total syntheses of schilancidilactones A and B, schilancitrilactone A, and 20-epi-schilancitrilactone A via late-stage nickel-catalyzed cross coupling.

Authors:  Hengtao Wang; Xiunan Zhang; Pingping Tang
Journal:  Chem Sci       Date:  2017-08-30       Impact factor: 9.825

5.  Biomimetically inspired asymmetric total synthesis of (+)-19-dehydroxyl arisandilactone A.

Authors:  Yi-Xin Han; Yan-Long Jiang; Yong Li; Hai-Xin Yu; Bing-Qi Tong; Zhe Niu; Shi-Jie Zhou; Song Liu; Yu Lan; Jia-Hua Chen; Zhen Yang
Journal:  Nat Commun       Date:  2017-01-31       Impact factor: 14.919

6.  Convergent Total Syntheses of (-)-Rubriflordilactone B and (-)-pseudo-Rubriflordilactone B.

Authors:  Mujahid Mohammad; Venkaiah Chintalapudi; Jeffrey M Carney; Steven J Mansfield; Pollyanna Sanderson; Kirsten E Christensen; Edward A Anderson
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-31       Impact factor: 15.336

7.  Total Synthesis of (+)-Rubriflordilactone A.

Authors:  Shermin S Goh; Guilhem Chaubet; Birgit Gockel; Marie-Caroline A Cordonnier; Hannah Baars; Andrew W Phillips; Edward A Anderson
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-04       Impact factor: 15.336

8.  Total Synthesis of the Schisandraceae Nortriterpenoid Rubriflordilactone A.

Authors:  Guilhem Chaubet; Shermin S Goh; Mujahid Mohammad; Birgit Gockel; Marie-Caroline A Cordonnier; Hannah Baars; Andrew W Phillips; Edward A Anderson
Journal:  Chemistry       Date:  2017-09-08       Impact factor: 5.236

Review 9.  Advances in the Asymmetric Total Synthesis of Natural Products Using Chiral Secondary Amine Catalyzed Reactions of α,β-Unsaturated Aldehydes.

Authors:  Zhonglei Wang
Journal:  Molecules       Date:  2019-09-19       Impact factor: 4.411

10.  Enantioselective Total Synthesis of (+)-Heilonine.

Authors:  Kyle J Cassaidy; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2021-09-29       Impact factor: 15.419

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