Literature DB >> 19655733

Total synthesis of (+/-)-kellermanoldione: stepwise cycloaddition of a functionalized diene and allenoate.

Michael E Jung1, Jesus Cordova, Masayuki Murakami.   

Abstract

The total synthesis of the diterpene kellermanoldione 1 is reported. Stepwise [4 + 2] cycloaddition of the ketal diene 8 and the allenoate 3 afforded the exo adduct 10x as the major product. It was converted into 1 via six steps, among them a key nonconjugative hydrolysis of a gamma-methylene silyl enol ether.

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Year:  2009        PMID: 19655733     DOI: 10.1021/ol901455q

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


  2 in total

1.  Allenoates in Enantioselective [2+2] Cycloadditions: From a Mechanistic Curiosity to a Stereospecific Transformation.

Authors:  Johannes M Wiest; Michael L Conner; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2018-11-05       Impact factor: 15.419

2.  Chiral Allenylcarbonyls - Underexploited Building Blocks for Complex Synthesis.

Authors:  Krishna Yadavalli; Salvatore D Lepore
Journal:  Lett Org Chem       Date:  2022-02-01       Impact factor: 0.797

  2 in total

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