Literature DB >> 19968244

Efficient asymmetric synthesis of abeo-abietane-type diterpenoids by using the intramolecular Heck reaction.

Manabu Node1, Minoru Ozeki, Loïc Planas, Masashi Nakano, Hirofumi Takita, Daisuke Mori, Shinji Tamatani, Tetsuya Kajimoto.   

Abstract

The synthesis of the abeo-abietane-type diterpenoids, i.e., (-)-dichroanal B, (-)-dichroanone, and taiwaniaquinone H, was achieved by using the intramolecular asymmetric Heck reaction. Our synthetic routes required fewer steps and gave a much higher overall yield and ee within shorter steps than those for racemic and antipodal forms reported to date (10, 12, and 13 steps with an overall yield of 50%, 40%, and 39%, and 94%, 98%, and 98% ee, respectively).

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Year:  2010        PMID: 19968244     DOI: 10.1021/jo901972b

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


  4 in total

1.  Ethylene in organic synthesis: a new route to anticholenergic pyrrolidinoindolines, and other molecules with all carbon-quaternary centers via asymmetric hydrovinylation.

Authors:  Hwan Jung Lim; T V RajanBabu
Journal:  Org Lett       Date:  2011-11-21       Impact factor: 6.005

2.  Enantioselective total syntheses of (-)-taiwaniaquinone H and (-)-taiwaniaquinol B by iridium-catalyzed borylation and palladium-catalyzed asymmetric α-arylation.

Authors:  Xuebin Liao; Levi M Stanley; John F Hartwig
Journal:  J Am Chem Soc       Date:  2011-01-26       Impact factor: 15.419

3.  A catalytic, enantioselective formal synthesis of (+)-dichroanone and (+)-taiwaniaquinone H.

Authors:  Samantha E Shockley; Jeffrey C Holder; Brian M Stoltz
Journal:  Org Lett       Date:  2014-12-09       Impact factor: 6.005

4.  Deconjugative α-Alkylation of Cyclohexenecarboxaldehydes: An Access to Diverse Terpenoids.

Authors:  Rachid Chahboun; José Manuel Botubol-Ares; María Jesús Durán-Peña; Fermín Jiménez; Ramón Alvarez-Manzaneda; Enrique Alvarez-Manzaneda
Journal:  J Org Chem       Date:  2021-06-15       Impact factor: 4.354

  4 in total

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