Literature DB >> 19245241

Total syntheses of enokipodins A and B utilizing palladium-catalyzed addition of an arylboronic acid to an allene.

Masahiro Yoshida1, Yasunobu Shoji, Kozo Shishido.   

Abstract

The enantioselective total syntheses of enokipodins A and B, alpha-cuparenone-type sesquiterpenoids with antimicrobial activity, have been achieved. The key step is the enantiospecific construction of the quaternary carbon center using a palladium-catalyzed addition of an arylboronic acid to an allene followed by an Eschenmoser-Claisen rearrangement.

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Year:  2009        PMID： 19245241     DOI： 10.1021/ol9001637

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


  7 in total

1.  Organo-manganese η2-auxiliary directed reactions: a diastereoselective approach to 2,3-allenols.

Authors:  Animesh Roy; Bilal A Bhat; Salvatore D Lepore
Journal:  Org Lett       Date:  2015-02-09       Impact factor: 6.005

2.  A density functional theory approach toward substituent effect in Meerwein-Eschenmoser-Claisen rearrangement.

Authors:  Rahim Ghadari; Ahmad Shaabani
Journal:  J Mol Model       Date:  2011-04-27       Impact factor: 1.810

3.  Structural determination of complex natural products by quantum mechanical calculations of (13)C NMR chemical shifts: development of a parameterized protocol for terpenes.

Authors:  Ana Carolina Ferreira de Albuquerque; Daniel Joras Ribeiro; Mauro Barbosa de Amorim
Journal:  J Mol Model       Date:  2016-07-16       Impact factor: 1.810

4.  Enantioselective construction of all-carbon quaternary centers by branch-selective Pd-catalyzed allyl-allyl cross-coupling.

Authors:  Ping Zhang; Hai Le; Robert E Kyne; James P Morken
Journal:  J Am Chem Soc       Date:  2011-06-07       Impact factor: 15.419

5.  A multicomponent Ni-, Zr-, and Cu-catalyzed strategy for enantioselective synthesis of alkenyl-substituted quaternary carbons.

Authors:  Kevin P McGrath; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2014-01-29       Impact factor: 15.336

6.  Use of P450 cytochrome inhibitors in studies of enokipodin biosynthesis.

Authors:  Noemia Kazue Ishikawa; Satoshi Tahara; Tomohiro Namatame; Afgan Farooq; Yukiharu Fukushi
Journal:  Braz J Microbiol       Date:  2014-03-10       Impact factor: 2.476

7.  A short synthesis of bisabolane sesquiterpenes.

Authors:  Zhen-Ting Du; Shuai Zheng; Gang Chen; Dong Lv
Journal:  Molecules       Date:  2011-09-19       Impact factor: 4.411
  7 in total

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