Literature DB >> 34324817

Total Synthesis of (-)-Strempeliopine.

Xianhuang Zeng1, Dale L Boger1.   

Abstract

A total synthesis of (-)-strempeliopine is disclosed that enlists a powerful SmI2-mediated and BF3·OEt2-initiated dearomative transannular radical cyclization onto an indole by an N-acyl α-aminoalkyl radical that is derived by single electron reduction of an in situ generated iminium ion for formation of a quaternary center and the strategic C19-C2 bond in its core structure.

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Year:  2021        PMID： 34324817      PMCID： PMC8405276          DOI： 10.1021/jacs.1c06913

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   16.383


  22 in total

1.  GENERAL METHODS OF SYNTHESIS OF INDOLE ALKALOIDS. IV. A SYNTHESIS OF DL-EBURNAMONINE.

Authors:  E WENKERT; B WICKBERG
Journal:  J Am Chem Soc       Date:  1965-04-05       Impact factor: 15.419

2.  Chemoselective N-acylation of indoles and oxazolidinones with carbonylazoles.

Authors:  Stephen T Heller; Erica E Schultz; Richmond Sarpong
Journal:  Angew Chem Int Ed Engl       Date:  2012-07-11       Impact factor: 15.336

3.  Studies on indole alkaloid biosynthesis. VI. The eburnamine-vincamine alkaloids.

Authors:  J P Kutney; J R Beck; V R Nelson; R S Sood
Journal:  J Am Chem Soc       Date:  1971-01-13       Impact factor: 15.419

4.  Next-Generation Total Synthesis of Vancomycin.

Authors:  Maxwell J Moore; Shiwei Qu; Ceheng Tan; Yu Cai; Yuzo Mogi; D Jamin Keith; Dale L Boger
Journal:  J Am Chem Soc       Date:  2020-09-04       Impact factor: 15.419

5.  One-pot reductive coupling of N-acylcarbamates with activated alkenes: application to the asymmetric synthesis of pyrrolo[1,2-a]azepin-5-one ring system and (-)-xenovenine.

Authors:  Xue-Kui Liu; Xiao Zheng; Yuan-Ping Ruan; Jie Ma; Pei-Qiang Huang
Journal:  Org Biomol Chem       Date:  2011-12-20       Impact factor: 3.876

6.  Selectivity in the Addition of Electron Deficient Radicals to the C2 Position of Indoles.

Authors:  Yi Li; Roy J Vaz; Steven H Olson; Mark Munson; Nick A Paras; Jay Conrad
Journal:  European J Org Chem       Date:  2020-08-18

7.  Application of cross-conjugated heteroaromatic betaines to the synthesis of the schizozygane alkaloid (+/-)-strempeliopine.

Authors:  Drew R Bobeck; Hyoung Ik Lee; Andrew C Flick; Albert Padwa
Journal:  J Org Chem       Date:  2009-10-02       Impact factor: 4.354

8.  Synthetic Utilization of α-Aminoalkyl Radicals and Related Species in Visible Light Photoredox Catalysis.

Authors:  Kazunari Nakajima; Yoshihiro Miyake; Yoshiaki Nishibayashi
Journal:  Acc Chem Res       Date:  2016-08-09       Impact factor: 22.384

9.  Tandem Intramolecular Diels-Alder/1,3-Dipolar Cycloaddition Cascade of 1,3,4-Oxadiazoles: Initial Scope and Applications.

Authors:  Justin E Sears; Dale L Boger
Journal:  Acc Chem Res       Date:  2016-01-27       Impact factor: 22.384

10.  Alkaloids from Roots of Strempeliopsis strempelioides - Structures of Strempeliopine and Strempeliopidine1.

Authors:  A Laguna; L Novotný; L Dolejs; M Budesínský
Journal:  Planta Med       Date:  1984-08       Impact factor: 3.352
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  2 in total

Review 1.  Samarium(ii) iodide-mediated reactions applied to natural product total synthesis.

Authors:  Majid M Heravi; Azadeh Nazari
Journal:  RSC Adv       Date:  2022-03-30       Impact factor: 3.361

2.  Asymmetric Total Synthesis of (-)-Phaeocaulisin A.

Authors:  Áron Péter; Giacomo E M Crisenza; David J Procter
Journal:  J Am Chem Soc       Date:  2022-04-13       Impact factor: 16.383
  2 in total

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