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Literature DB >> 24825410

Synthesis of tetrahydropyran/tetrahydrofuran-containing macrolides by palladium-catalyzed alkoxycarbonylative macrolactonizations.

Abstract

A novel Pd-catalyzed cascade alkoxycarbonylative macrolactonization to construct tetrahydropyran/tetrahydrofuran-containing bridged macrolactones in one step from alkendiols is described. Products with various ring sizes and substituents were obtained. Challenging macrolactones involving tertiary alcohols were synthesized smoothly as well. Mechanistically, experimental evidence to support a trans-oxypalladation step has been provided. The method was applied to the synthesis of potent anticancer compound 9-demethylneopeltolide.

Entities: Chemical Disease Species

Keywords: carbonylation; macrolactonization; macrolide; neopeltolide; palladium

Mesh：

Substances：

Year: 2014 PMID： 24825410 PMCID： PMC4126560 DOI： 10.1002/anie.201403006

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

57 in total

1. Concise formal synthesis of (+)-neopeltolide.

Authors: Zhen Yang; Bingbin Zhang; Gaoyuan Zhao; Juan Yang; Xingang Xie; Xuegong She
Journal: Org Lett Date: 2011-10-13 Impact factor: 6.005

2. Total synthesis of (+)-neopeltolide.

Authors: Haruhiko Fuwa; Shinya Naito; Tomomi Goto; Makoto Sasaki
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

Review 3. The exploration of macrocycles for drug discovery--an underexploited structural class.

Authors: Edward M Driggers; Stephen P Hale; Jinbo Lee; Nicholas K Terrett
Journal: Nat Rev Drug Discov Date: 2008-07 Impact factor: 84.694

4. Diastereoselective total synthesis of (±)-schindilactone A.

Authors: Qing Xiao; Wei-Wu Ren; Zhi-Xing Chen; Tian-Wen Sun; Yong Li; Qin-Da Ye; Jian-Xian Gong; Fan-Ke Meng; Lin You; Yi-Fan Liu; Ming-Zhe Zhao; Ling-Min Xu; Zhen-Hua Shan; Ying Shi; Ye-Feng Tang; Jia-Hua Chen; Zhen Yang
Journal: Angew Chem Int Ed Engl Date: 2011-07-07 Impact factor: 15.336

5. Total synthesis and structure-activity investigation of the marine natural product neopeltolide.

Authors: Daniel W Custar; Thomas P Zabawa; John Hines; Craig M Crews; Karl A Scheidt
Journal: J Am Chem Soc Date: 2009-09-02 Impact factor: 15.419

6. Neopeltolide, a macrolide from a lithistid sponge of the family Neopeltidae.

Authors: Amy E Wright; Julianne Cook Botelho; Esther Guzmán; Dedra Harmody; Patricia Linley; Peter J McCarthy; Tara P Pitts; Shirley A Pomponi; John K Reed
Journal: J Nat Prod Date: 2007-02-20 Impact factor: 4.050

7. Synthesis and biological evaluation of neopeltolide and analogs.

Authors: Yubo Cui; Raghavan Balachandran; Billy W Day; Paul E Floreancig
Journal: J Org Chem Date: 2012-02-22 Impact factor: 4.354

8. Total synthesis and structural revision of the marine macrolide neopeltolide.

Authors: Daniel W Custar; Thomas P Zabawa; Karl A Scheidt
Journal: J Am Chem Soc Date: 2008-01-23 Impact factor: 15.419

9. Total synthesis and biological activity of neopeltolide and analogues.

Authors: Viktor V Vintonyak; Brigitte Kunze; Florenz Sasse; Martin E Maier
Journal: Chemistry Date: 2008 Impact factor: 5.236

10. Lyngbyaloside B, a new glycoside macrolide from a Palauan marine cyanobacterium, Lyngbya sp.

Authors: Hendrik Luesch; Wesley Y Yoshida; George G Harrigan; James P Doom; Richard E Moore; Valerie J Paul
Journal: J Nat Prod Date: 2002-12 Impact factor: 4.050

11 in total

1. 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

2. Exo-selective reductive macrocyclization of ynals.

Authors: Hengbin Wang; Solymar Negretti; Allison R Knauff; John Montgomery
Journal: Org Lett Date: 2015-03-06 Impact factor: 6.005

3. Recent Developments in Pd(0)-Catalyzed Alkene Carboheterofunctionalization Reactions.

Authors: Zachary J Garlets; Derick R White; John P Wolfe
Journal: Asian J Org Chem Date: 2017-03-10 Impact factor: 3.319

4. Total Synthesis and Structural Reassignment of Lyngbyaloside C Highlighted by Intermolecular Ketene Esterification.

Authors: Chia-Fu Chang; Eric Stefan; Richard E Taylor
Journal: Chemistry Date: 2015-06-23 Impact factor: 5.236

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. Rapid synthesis of bicyclic lactones via palladium-catalyzed aminocarbonylative lactonizations.

Authors: Xianglin Yin; Haroon Mohammad; Hassan E Eldesouky; Ahmed Abdelkhalek; Mohamed N Seleem; Mingji Dai
Journal: Chem Commun (Camb) Date: 2017-06-29 Impact factor: 6.222

7. Catalytic Carbonylative Spirolactonization of Hydroxycyclopropanols.

Authors: Dexter C Davis; Katherine L Walker; Chunhua Hu; Richard N Zare; Robert M Waymouth; Mingji Dai
Journal: J Am Chem Soc Date: 2016-08-11 Impact factor: 15.419

8. Strategies and Methods for the Synthesis of Anticancer Natural Product Neopeltolide and its Analogs.

Authors: Yu Bai; Mingji Dai
Journal: Curr Org Chem Date: 2015 Impact factor: 2.180

9. Total Synthesis of (-)-Spinosyn A via Carbonylative Macrolactonization.

Authors: Yu Bai; Xingyu Shen; Yong Li; Mingji Dai
Journal: J Am Chem Soc Date: 2016-08-17 Impact factor: 15.419

Review 10. Contemporary Strategies for the Synthesis of Tetrahydropyran Derivatives: Application to Total Synthesis of Neopeltolide, a Marine Macrolide Natural Product.

Authors: Haruhiko Fuwa
Journal: Mar Drugs Date: 2016-03-25 Impact factor: 5.118