Literature DB >> 12735765

Catalytic crossed Michael cycloisomerization of thioenoates: total synthesis of (+/-)-ricciocarpin A.

Kyriacos Agapiou1, Michael J Krische.   

Abstract

[reaction: see text] Thioenoates are found to participate in highly chemoselective catalytic crossed Michael cycloisomerization with appendant aryl ketone and enoate partners to afford cyclopentene and cyclohexene products. This methodology has enabled a concise total synthesis of the potent molluscicide (+/-)-ricciocarpin A.

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Year:  2003        PMID： 12735765     DOI： 10.1021/ol030035e

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


  10 in total

1.  Quasi-Biomimetic Ring Contraction Catalyzed by a Cysteine-Based Nucleophile: Total Synthesis of Sch-642305, Some Analogs and their Putative anti-HIV Activities.

Authors:  Alpay Dermenci; Philipp S Selig; Robert A Domaoal; Krasimir A Spasov; Karen S Anderson; Scott J Miller
Journal:  Chem Sci       Date:  2011-08-01       Impact factor: 9.825

2.  Concise synthesis of ricciocarpin A and discovery of a more potent analogue.

Authors:  Anna Michrowska; Benjamin List
Journal:  Nat Chem       Date:  2009-05-22       Impact factor: 24.427

3.  Nucleophilic Chiral Phosphines: Powerful and Versatile Catalysts for Asymmetric Annulations.

Authors:  Yumei Xiao; Hongchao Guo; Ohyun Kwon
Journal:  Aldrichimica Acta       Date:  2016       Impact factor: 3.667

4.  Remarkable phosphine-effect on the intramolecular aldol reactions of unsaturated 1,5-diketones: highly regioselective synthesis of cross-conjugated dienones.

Authors:  Reema K Thalji; William R Roush
Journal:  J Am Chem Soc       Date:  2005-12-07       Impact factor: 15.419

5.  Total synthesis of cyanolide A in the absence of protecting groups, chiral auxiliaries, or premetalated carbon nucleophiles.

Authors:  Andrew R Waldeck; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2013-03-11       Impact factor: 15.336

6.  Lewis acid-catalyzed conjugate additions of silyloxyallenes: a selective solution to the intermolecular Rauhut-Currier problem.

Authors:  Troy E Reynolds; Michael S Binkley; Karl A Scheidt
Journal:  Org Lett       Date:  2008-05-14       Impact factor: 6.005

7.  Asymmetric total synthesis of the iridoid beta-glucoside (+)-geniposide via phosphine organocatalysis.

Authors:  Regan A Jones; Michael J Krische
Journal:  Org Lett       Date:  2009-04-16       Impact factor: 6.005

8.  One-pot odourless synthesis of thioesters via in situ generation of thiobenzoic acids using benzoic anhydrides and thiourea.

Authors:  Mohammad Abbasi; Reza Khalifeh
Journal:  Beilstein J Org Chem       Date:  2015-07-28       Impact factor: 2.883

9.  Phosphine-Promoted [4 + 3] Annulation of Allenoate with Aziridines for Synthesis of Tetrahydroazepines: Phosphine-Dependent [3 + 3] and [4 + 3] Pathways.

Authors:  Honglei Liu; Yan Lin; Yan Zhao; Miaoren Xiao; Leijie Zhou; Qijun Wang; Cheng Zhang; Dongqi Wang; Ohyun Kwon; Hongchao Guo
Journal:  RSC Adv       Date:  2019-01-09       Impact factor: 4.036

10.  S-Phenyl 4-meth-oxy-benzothio-ate.

Authors:  Adel S El-Azab; Alaa A-M Abdel-Aziz; Hussein I El-Subbagh; Suchada Chantrapromma; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-03-17
  10 in total

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