Literature DB >> 30760840

Total Synthesis of trans-Resorcylide via Macrocyclic Stille Carbonylation.

Yiyang Luo1, Xianglin Yin1, Mingji Dai2.   

Abstract

The resorcylic macrolides are important natural products with a wide range of remarkable biological activities. So far, most of the reported resorcylic macrolide syntheses use either macrolactonization or ring closing metathesis to build the corresponding macrocycle. In continuation of our efforts in developing novel carbonylation reactions to facilitate natural product total synthesis, we report herein a total synthesis of trans-resorcylide (1) featuring a palladium-catalyzed macrocyclic Stille carbonylation to build its 12-membered macrocycle.

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Year:  2019        PMID: 30760840      PMCID: PMC7063981          DOI: 10.1038/s41429-019-0145-4

Source DB:  PubMed          Journal:  J Antibiot (Tokyo)        ISSN: 0021-8820            Impact factor:   2.649


  20 in total

1.  Efficient asymmetric synthesis of radicicol dimethyl ether: a novel application of ring-forming olefin metathesis.

Authors:  R M Garbaccio; S J Danishefsky
Journal:  Org Lett       Date:  2000-10-05       Impact factor: 6.005

2.  Total synthesis as a resource in the discovery of potentially valuable antitumor agents: cycloproparadicicol.

Authors:  Kana Yamamoto; Robert M Garbaccio; Shawn J Stachel; David B Solit; Gabriela Chiosis; Neal Rosen; Samuel J Danishefsky
Journal:  Angew Chem Int Ed Engl       Date:  2003-03-17       Impact factor: 15.336

Review 3.  Natural product syntheses via carbonylative cyclizations.

Authors:  Kaiqing Ma; Brandon S Martin; Xianglin Yin; Mingji Dai
Journal:  Nat Prod Rep       Date:  2018-06-20       Impact factor: 13.423

4.  Total Syntheses of Bisdehydroneostemoninine and Bisdehydrostemoninine by Catalytic Carbonylative Spirolactonization.

Authors:  Kaiqing Ma; Xianglin Yin; Mingji Dai
Journal:  Angew Chem Int Ed Engl       Date:  2018-10-18       Impact factor: 15.336

5.  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

6.  Diastereoselective Intramolecular Carbolithiations of Stereodefined Secondary Alkyllithiums Bearing a Remote Alkynylsilane.

Authors:  Meike Simon; Konstantin Karaghiosoff; Paul Knochel
Journal:  Org Lett       Date:  2018-06-06       Impact factor: 6.005

7.  Natural Product Synthesis via Palladium-Catalyzed Carbonylation.

Authors:  Yu Bai; Dexter C Davis; Mingji Dai
Journal:  J Org Chem       Date:  2017-02-13       Impact factor: 4.354

8.  Development of a bio-inspired acyl-anion equivalent macrocyclization and synthesis of a trans-resorcylide precursor.

Authors:  Steven M Mennen; Scott J Miller
Journal:  J Org Chem       Date:  2007-06-19       Impact factor: 4.354

9.  Unconventional Fragment Usage Enables a Concise Total Synthesis of (-)-Callyspongiolide.

Authors:  Francesco Manoni; Corentin Rumo; Liubo Li; Patrick G Harran
Journal:  J Am Chem Soc       Date:  2018-01-19       Impact factor: 15.419

Review 10.  Development of purine-scaffold small molecule inhibitors of Hsp90.

Authors:  Gabriela Chiosis; Brian Lucas; Henri Huezo; David Solit; Andrea Basso; Neal Rosen
Journal:  Curr Cancer Drug Targets       Date:  2003-10       Impact factor: 3.428

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