Literature DB >> 18412344

The total synthesis of roquefortine C and a rationale for the thermodynamic stability of isoroquefortine C over roquefortine C.

Ning Shangguan1, Warren J Hehre, William S Ohlinger, Mary Pat Beavers, Madeleine M Joullié.   

Abstract

The first total synthesis of roquefortine C is achieved by implementation of a novel elimination strategy to construct the thermodynamically unstable E-dehydrohistidine moiety. Molecular modeling studies are presented which explain the instability of the roquefortine C structure compared to that of isoroquefortine C.

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Year:  2008        PMID: 18412344     DOI: 10.1021/ja800067q

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  8 in total

1.  Incorporating Fermentation into Undergraduate Laboratory Courses.

Authors:  Claire Gober; Madeleine Joullie
Journal:  Athens J Sci       Date:  2015-12

2.  A Copper-Carbodiimide Approach to the Phomopsin Tripeptide Side Chain.

Authors:  Ning Shangguan; Madeleine Joullié
Journal:  Tetrahedron Lett       Date:  2009-12-09       Impact factor: 2.415

3.  Total Synthesis of Isoroquefortine E and Phenylahistin.

Authors:  Ning Shangguan; Madeleine Joullié
Journal:  Tetrahedron Lett       Date:  2009-12-09       Impact factor: 2.415

4.  Protecting-group-free synthesis of 3-tert-prenylated oxindoles: contiguous all-carbon quaternary centers via tertiary neopentyl substitution.

Authors:  Christopher D Grant; Michael J Krische
Journal:  Org Lett       Date:  2009-10-15       Impact factor: 6.005

5.  OxaD: A Versatile Indolic Nitrone Synthase from the Marine-Derived Fungus Penicillium oxalicum F30.

Authors:  Sean A Newmister; Claire M Gober; Stelamar Romminger; Fengan Yu; Ashootosh Tripathi; Lizbeth Lorena L Parra; Robert M Williams; Roberto G S Berlinck; Madeleine M Joullié; David H Sherman
Journal:  J Am Chem Soc       Date:  2016-08-24       Impact factor: 15.419

Review 6.  Joining Forces: Fermentation and Organic Synthesis for the Production of Complex Heterocycles.

Authors:  Claire M Gober; Madeleine M Joullié
Journal:  J Org Chem       Date:  2016-07-28       Impact factor: 4.354

7.  Synthesis of monoalkylidene diketopiperazines and application to the synthesis of barettin.

Authors:  Elizabeth W Kelley; Skylar G Norman; Jonathan R Scheerer
Journal:  Org Biomol Chem       Date:  2017-10-18       Impact factor: 3.876

8.  Dearomative Indole (3 + 2) Reactions with Azaoxyallyl Cations--New Method for the Synthesis of Pyrroloindolines.

Authors:  Maria C DiPoto; Russell P Hughes; Jimmy Wu
Journal:  J Am Chem Soc       Date:  2015-11-17       Impact factor: 15.419

  8 in total

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