Literature DB >> 18771326

Synthesis of (-)-hamigeran B.

Douglass F Taber1, Weiwei Tian.   

Abstract

The synthesis of (-)-hamigeran B has been achieved, based on a new approach to cyclopentane construction, the rhodium-mediated intramolecular C-H insertion of alpha-aryl-alpha-diazoketones. The endo-isopropyl group was installed by selective hydrogenation of a cyclopropylidene substituent.

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Year:  2008        PMID： 18771326      PMCID： PMC2626181          DOI： 10.1021/jo8010683

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


  12 in total

1.  Total Synthesis of Hamigerans: Part 2. Implementation of the Intramolecular Diels-Alder Trapping of Photochemically Generated Hydroxy-o-quinodimethanes; Strategy and Completion of the Synthesis This work was financially supported by the National Institutes of Health (USA) and The Skaggs Institute for Chemical Biology, and grants from Abbott, Amgen, ArrayBiopharma, Boehringer-Ingelheim, Glaxo, Hoffmann-La Roche, DuPont, Merck, Pfizer, and Schering Plough.

Authors:  K. C. Nicolaou; David Gray; Jinsung Tae
Journal:  Angew Chem Int Ed Engl       Date:  2001-10-01       Impact factor: 15.336

2.  Stereospecific total synthesis of the antiviral agent hamigeran B--use of large silyl groups to enforce facial selectivity and to suppress hydrogenolysis.

Authors:  Derrick L J Clive; Jian Wang
Journal:  Angew Chem Int Ed Engl       Date:  2003-07-28       Impact factor: 15.336

3.  Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion.

Authors:  Huw M L Davies; Rohan E J Beckwith
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

4.  Catalytic and enantioselective allylic C-H activation with donor-acceptor-substituted carbenoids.

Authors:  Huw M L Davies; Joachim Nikolai
Journal:  Org Biomol Chem       Date:  2005-10-31       Impact factor: 3.876

5.  A short and concise asymmetric synthesis of hamigeran B.

Authors:  Barry M Trost; Carole Pissot-Soldermann; Irwin Chen
Journal:  Chemistry       Date:  2005-01-21       Impact factor: 5.236

6.  Synthesis of (+)-sulcatine G.

Authors:  Douglass F Taber; Kevin J Frankowski
Journal:  J Org Chem       Date:  2005-08-05       Impact factor: 4.354

7.  Rhodium-catalyzed intramolecular C-H insertion of alpha-aryl-alpha-diazo ketones.

Authors:  Douglass F Taber; Weiwei Tian
Journal:  J Org Chem       Date:  2007-03-27       Impact factor: 4.354

8.  Synthesis of (+/-)-hamigeran B, (-)-hamigeran B, and (+/-)-1-epi-hamigeran B: use of bulky silyl groups to protect a benzylic carbon-oxygen bond from hydrogenolysis.

Authors:  Derrick L J Clive; Jian Wang
Journal:  J Org Chem       Date:  2004-04-16       Impact factor: 4.354

9.  An asymmetric synthesis of hamigeran B via a Pd asymmetric allylic alkylation for enantiodiscrimination.

Authors:  Barry M Trost; Carole Pissot-Soldermann; Irwin Chen; Gretchen M Schroeder
Journal:  J Am Chem Soc       Date:  2004-04-14       Impact factor: 15.419

10.  Total synthesis of hamigerans and analogues thereof. Photochemical generation and Diels-Alder trapping of hydroxy-o-quinodimethanes.

Authors:  K C Nicolaou; David L F Gray; Jinsung Tae
Journal:  J Am Chem Soc       Date:  2004-01-21       Impact factor: 15.419
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  10 in total

1.  A catalytic, asymmetric formal synthesis of (+)-hamigeran B.

Authors:  Herschel Mukherjee; Nolan T McDougal; Scott C Virgil; Brian M Stoltz
Journal:  Org Lett       Date:  2011-01-27       Impact factor: 6.005

2.  Aliphatic C-H to C-C conversion: synthesis of (-)-cameroonan-7α-ol.

Authors:  Douglass F Taber; Christopher G Nelson
Journal:  J Org Chem       Date:  2011-02-23       Impact factor: 4.354

3.  Synthetic Studies toward the Hamigerans with a 6-7-5 Tricyclic Core.

Authors:  Baiyang Jiang; Mingji Dai
Journal:  Org Lett       Date:  2020-05-13       Impact factor: 6.005

4.  11-Step and Scalable Total Synthesis of Hamigeran M Enabled by Five C-H Functionalizations.

Authors:  Baiyang Jiang; Mingji Dai
Journal:  J Am Chem Soc       Date:  2021-11-23       Impact factor: 16.383

Review 5.  Application of donor/acceptor-carbenoids to the synthesis of natural products.

Authors:  Huw M L Davies; Justin R Denton
Journal:  Chem Soc Rev       Date:  2009-09-30       Impact factor: 54.564

6.  The combined C-H functionalization/Cope rearrangement: discovery and applications in organic synthesis.

Authors:  Huw M L Davies; Yajing Lian
Journal:  Acc Chem Res       Date:  2012-05-11       Impact factor: 22.384

Review 7.  Cross-coupling reactions towards the synthesis of natural products.

Authors:  Shaheera Tabassum; Ameer Fawad Zahoor; Sajjad Ahmad; Razia Noreen; Samreen Gul Khan; Hamad Ahmad
Journal:  Mol Divers       Date:  2021-02-20       Impact factor: 2.943

8.  Progress towards the total synthesis of hamigerans C and D: a direct approach to an elaborated 6-7-5 carbocyclic core.

Authors:  Douglas Charles Duquette; Thomas Jensen; Brian Mark Stoltz
Journal:  J Antibiot (Tokyo)       Date:  2017-09-06       Impact factor: 2.649

9.  Synthesis of Vicinal Carbocycles by Intramolecular Nickel-Catalyzed Conjunctive Cross-Electrophile Coupling Reaction.

Authors:  Kirsten A Hewitt; Claire A Herbert; Elizabeth R Jarvo
Journal:  Org Lett       Date:  2022-08-04       Impact factor: 6.072

10.  Synthesis and Biological Evaluation of Diversified Hamigeran B Analogs as Neuroinflammatory Inhibitors and Neurite Outgrowth Stimulators.

Authors:  Ruo-Xin Li; Rui Han; Guo-Jie Wu; Fu-She Han; Jin-Ming Gao
Journal:  Mar Drugs       Date:  2020-06-11       Impact factor: 5.118
  10 in total

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