Literature DB >> 23106671

Toward the total synthesis of (±)-andrastin C.

Rei Okamoto1, Kazutaka Takeda, Hidetoshi Tokuyama, Masataka Ihara, Masahiro Toyota.   

Abstract

An efficient approach to generate a fully functionalized cyclopenta[a]phenanthrene 34, the basic carbon framework of andrastin C (1c), is described. The present synthetic route features a stereoselective intramolecular Diels-Alder reaction of triene 12 and an intramolecular carbonyl ene reaction of 3-phenanthrenyl-2-(methoxymethoxy)propanal 31.

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Year:  2012        PMID： 23106671     DOI： 10.1021/jo301948h

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  3 in total

1.  Traversing Biosynthetic Carbocation Landscapes in the Total Synthesis of Andrastin and Terretonin Meroterpenes.

Authors:  Gong Xu; Masha Elkin; Dean J Tantillo; Timothy R Newhouse; Thomas J Maimone
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-30       Impact factor: 15.336

2.  Meroterpenoid Synthesis via Sequential Polyketide Aromatization and Radical Anion Cascade Triene Cyclization: Biomimetic Total Syntheses of Austalide Natural Products.

Authors:  Tsz-Kan Ma; Philip J Parsons; Anthony G M Barrett
Journal:  J Org Chem       Date:  2019-04-04       Impact factor: 4.354

3.  Enantioselective total syntheses of FR901464 and spliceostatin A and evaluation of splicing activity of key derivatives.

Authors:  Arun K Ghosh; Zhi-Hua Chen; Kerstin A Effenberger; Melissa S Jurica
Journal:  J Org Chem       Date:  2014-05-30       Impact factor: 4.354
  3 in total

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