Literature DB >> 17579456

Asymmetric total synthesis of (-)-Linderol A.

Masayuki Yamashita1, Navnath Dnyanoba Yadav, Takeshi Sawaki, Ikuko Takao, Ikuo Kawasaki, Yasuko Sugimoto, Akemi Miyatake, Kousuke Murai, Ayano Takahara, Ai Kurume, Shunsaku Ohta.   

Abstract

The first asymmetric total synthesis of (-)-Linderol A, a potent inhibitor of melanin biosynthesis of cultured B-16 melanoma cells, has been achieved via two key reactions: a diastereoselective [2+2] photocycloaddition of a coumarin-3-carboxylate bearing a chiral auxiliary with 3-methyl-1-butene and a subsequent stereoconvergent transformation of the photoadducts with use of dimethylsulfoxonium methylide to afford a tetrahydrodibenzofuran derivative.

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Year:  2007        PMID: 17579456     DOI: 10.1021/jo070682+

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


  3 in total

1.  Divergent Reactivity during the Trapping of Benzynes by Glycidol Analogs: Ring Cleavage via Pinacol-Like Rearrangements vs Oxirane Fragmentations.

Authors:  Juntian Zhang; Thomas R Hoye
Journal:  Org Lett       Date:  2019-04-10       Impact factor: 6.005

2.  Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions.

Authors:  Saner Poplata; Andreas Tröster; You-Quan Zou; Thorsten Bach
Journal:  Chem Rev       Date:  2016-03-28       Impact factor: 60.622

Review 3.  Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis.

Authors:  Markus D Kärkäs; John A Porco; Corey R J Stephenson
Journal:  Chem Rev       Date:  2016-04-27       Impact factor: 60.622

  3 in total

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