Literature DB >> 19943699

Expedient construction of the Ziegler intermediate useful for the synthesis of forskolin via consecutive rearrangements.

Heping Ye1, Gang Deng, Jun Liu, Fayang G Qiu.   

Abstract

The Ziegler intermediate, useful for the total synthesis of forskolin, was synthesized in 10 reaction steps starting from commercially available alpha-ionone. This highly efficient synthesis relies on the success of two consecutive highly regio- and stereoselective rearrangements. The current synthesis has not only established an efficient synthetic route to access the Ziegler intermediate but it has also paved a way to the structural optimization of forskolin.

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Year:  2009        PMID: 19943699     DOI: 10.1021/ol902133q

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  3 in total

1.  Manoyl oxide (13R), the biosynthetic precursor of forskolin, is synthesized in specialized root cork cells in Coleus forskohlii.

Authors:  Irini Pateraki; Johan Andersen-Ranberg; Britta Hamberger; Allison Maree Heskes; Helle Juel Martens; Philipp Zerbe; Søren Spanner Bach; Birger Lindberg Møller; Jörg Bohlmann; Björn Hamberger
Journal:  Plant Physiol       Date:  2014-01-30       Impact factor: 8.340

2.  Two-step synthesis of chiral fused tricyclic scaffolds from phenols via desymmetrization on nickel.

Authors:  Ravindra Kumar; Yoichi Hoshimoto; Eri Tamai; Masato Ohashi; Sensuke Ogoshi
Journal:  Nat Commun       Date:  2017-06-26       Impact factor: 14.919

3.  Total biosynthesis of the cyclic AMP booster forskolin from Coleus forskohlii.

Authors:  Irini Pateraki; Johan Andersen-Ranberg; Niels Bjerg Jensen; Sileshi Gizachew Wubshet; Allison Maree Heskes; Victor Forman; Björn Hallström; Britta Hamberger; Mohammed Saddik Motawia; Carl Erik Olsen; Dan Staerk; Jørgen Hansen; Birger Lindberg Møller; Björn Hamberger
Journal:  Elife       Date:  2017-03-14       Impact factor: 8.140

  3 in total

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