Literature DB >> 29711010

The Total Synthesis of Spirotryprostatin A.

Scott D Edmondson1, Samuel J Danishefsky1.   

Abstract

Eight concise steps suffice for the first total synthesis of the title compound 1, which inhibits the transitions from the G2 and M phases into the next phases of the cell cycle. Key steps in the synthesis are a stereocontrolled oxidative rearrangement of an indole to form the chiral spiroindolinone nucleus and a regioselecitve sulfoxide elimination. © 1998 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany.

Entities:  

Keywords:  2-oxindoles; Diketopiperazines; Spiro compounds; Spirotryprostatin A; Total synthesis

Year:  1998        PMID： 29711010     DOI： 10.1002/(SICI)1521-3773(19980504)37:8<1138::AID-ANIE1138>3.0.CO;2-N

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


  6 in total

1.  Terminating Catalytic Asymmetric Heck Cyclizations by Stereoselective Intramolecular Capture of η-Allylpalladium Intermediates: Total Synthesis of (-)-Spirotryprostatin B and Three Stereoisomers.

Authors:  Larry E Overman; Mark D Rosen
Journal:  Tetrahedron       Date:  2010-08-14       Impact factor: 2.457

2.  Chiral Brønsted base-promoted nitroalkane alkylation: enantioselective synthesis of sec-alkyl-3-substituted indoles.

Authors:  Mark C Dobish; Jeffrey N Johnston
Journal:  Org Lett       Date:  2010-11-19       Impact factor: 6.005

Review 3.  Natural products synthesis: enabling tools to penetrate Nature's secrets of biogenesis and biomechanism.

Authors:  Robert M Williams
Journal:  J Org Chem       Date:  2011-04-12       Impact factor: 4.354

4.  Synthesis, Biological and In Silico Evaluation of Pure Nucleobase-Containing Spiro (Indane-Isoxazolidine) Derivatives as Potential Inhibitors of MDM2-p53 Interaction.

Authors:  Loredana Maiuolo; Vincenzo Algieri; Beatrice Russo; Matteo Antonio Tallarida; Monica Nardi; Maria Luisa Di Gioia; Zahra Merchant; Pedro Merino; Ignacio Delso; Antonio De Nino
Journal:  Molecules       Date:  2019-08-10       Impact factor: 4.411

5.  Spiro[pyrrolidine-3, 3´-oxindole] as potent anti-breast cancer compounds: Their design, synthesis, biological evaluation and cellular target identification.

Authors:  Santanu Hati; Sayantan Tripathy; Pratip Kumar Dutta; Rahul Agarwal; Ramprasad Srinivasan; Ashutosh Singh; Shailja Singh; Subhabrata Sen
Journal:  Sci Rep       Date:  2016-08-30       Impact factor: 4.379

6.  Spiro[pyrrolidine-3,3'-oxindoles] and Their Indoline Analogues as New 5-HT6 Receptor Chemotypes.

Authors:  Ádám A Kelemen; Grzegorz Satala; Andrzej J Bojarski; György M Keserű
Journal:  Molecules       Date:  2017-12-14       Impact factor: 4.411
  6 in total

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