Literature DB >> 20462237

Synthesis of (+/-)-nosyberkol (isotuberculosinol, revised structure of edaxadiene) and (+/-)-tuberculosinol.

Nathan Maugel1, Francis M Mann, Matthew L Hillwig, Reuben J Peters, Barry B Snider.   

Abstract

Me(2)AlCl-catalyzed Diels-Alder reaction of N-tigloyloxazolidinone with 6,6-dimethyl-1-vinylcyclohexene selectively provided the exo adduct, which was converted to nosyberkol (isotuberculosinol) and tuberculosinol. The spectral data for nosyberkol are identical with those reported for edaxadiene, whose structure is revised accordingly.

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Year:  2010        PMID： 20462237      PMCID： PMC2880386          DOI： 10.1021/ol100832h

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


  8 in total

1.  Mycobacterium tuberculosis H37Rv3377c encodes the diterpene cyclase for producing the halimane skeleton.

Authors:  Chiaki Nakano; Tomoo Okamura; Tsutomu Sato; Tohru Dairi; Tsutomu Hoshino
Journal:  Chem Commun (Camb)       Date:  2005-01-04       Impact factor: 6.222

2.  Solid-phase synthesis of dysidiolide-derived protein phosphatase inhibitors.

Authors:  Dirk Brohm; Nicolas Philippe; Susanne Metzger; Ajay Bhargava; Oliver Müller; Folker Lieb; Herbert Waldmann
Journal:  J Am Chem Soc       Date:  2002-11-06       Impact factor: 15.419

3.  Asmarines I, J, and K and nosyberkol: four new compounds from the marine sponge Raspailia sp.

Authors:  Amira Rudi; Maurice Aknin; Emile Gaydou; Yoel Kashman
Journal:  J Nat Prod       Date:  2004-11       Impact factor: 4.050

4.  Enantioselective synthesis of alpha,beta-disubstituted-beta-amino acids.

Authors:  Mukund P Sibi; Narayanasamy Prabagaran; Sandeep G Ghorpade; Craig P Jasperse
Journal:  J Am Chem Soc       Date:  2003-10-01       Impact factor: 15.419

5.  Synthesis of (-)-nakamurol A and assignment of absolute configuration of diterpenoid (+)-nakamurol A.

Authors:  Sandra Díaz; Javier Cuesta; Asensio González; Josep Bonjoch
Journal:  J Org Chem       Date:  2003-09-19       Impact factor: 4.354

6.  Isolation of Mycobacterium tuberculosis mutants defective in the arrest of phagosome maturation.

Authors:  Kevin Pethe; Dana L Swenson; Sylvie Alonso; Jennifer Anderson; Carren Wang; David G Russell
Journal:  Proc Natl Acad Sci U S A       Date:  2004-08-31       Impact factor: 11.205

7.  Edaxadiene: a new bioactive diterpene from Mycobacterium tuberculosis.

Authors:  Francis M Mann; Meimei Xu; Xiaoming Chen; D Bruce Fulton; David G Russell; Reuben J Peters
Journal:  J Am Chem Soc       Date:  2009-12-09       Impact factor: 15.419

8.  Characterization and inhibition of a class II diterpene cyclase from Mycobacterium tuberculosis: implications for tuberculosis.

Authors:  Francis M Mann; Sladjana Prisic; Huayou Hu; Meimei Xu; Robert M Coates; Reuben J Peters
Journal:  J Biol Chem       Date:  2009-07-02       Impact factor: 5.157
  8 in total
  13 in total

1.  Stereoselective Synthesis of 1-Tuberculosinyl Adenosine; a Virulence Factor of Mycobacterium tuberculosis.

Authors:  Jeffrey Buter; Dorus Heijnen; Ieng Chim Wan; F Matthias Bickelhaupt; David C Young; Edwin Otten; D Branch Moody; Adriaan J Minnaard
Journal:  J Org Chem       Date:  2016-07-26       Impact factor: 4.354

2.  A novel labda-7,13e-dien-15-ol-producing bifunctional diterpene synthase from Selaginella moellendorffii.

Authors:  Sibongile Mafu; Matthew L Hillwig; Reuben J Peters
Journal:  Chembiochem       Date:  2011-07-12       Impact factor: 3.164

Review 3.  Bacterial diterpene synthases: new opportunities for mechanistic enzymology and engineered biosynthesis.

Authors:  Michael J Smanski; Ryan M Peterson; Sheng-Xiong Huang; Ben Shen
Journal:  Curr Opin Chem Biol       Date:  2012-03-22       Impact factor: 8.822

4.  Synthesis enables a structural revision of the Mycobacterium tuberculosis-produced diterpene, edaxadiene.

Authors:  Jillian E Spangler; Cheryl A Carson; Erik J Sorensen
Journal:  Chem Sci       Date:  2010-06-11       Impact factor: 9.825

5.  Magnesium depletion triggers production of an immune modulating diterpenoid in Mycobacterium tuberculosis.

Authors:  Francis M Mann; Brian C VanderVen; Reuben J Peters
Journal:  Mol Microbiol       Date:  2011-01-25       Impact factor: 3.501

6.  Genetics of Capsular Polysaccharides and Cell Envelope (Glyco)lipids.

Authors:  Mamadou Daffé; Dean C Crick; Mary Jackson
Journal:  Microbiol Spectr       Date:  2014

7.  Extreme promiscuity of a bacterial and a plant diterpene synthase enables combinatorial biosynthesis.

Authors:  Meirong Jia; Kevin C Potter; Reuben J Peters
Journal:  Metab Eng       Date:  2016-04-07       Impact factor: 9.783

8.  Isotuberculosinol: the unusual case of an immunomodulatory diterpenoid from Mycobacterium tuberculosis.

Authors:  Francis M Mann; Reuben J Peters
Journal:  Medchemcomm       Date:  2012-08-01       Impact factor: 3.597

9.  Design and Synthesis of Molecular Scaffolds with Anti-infective Activity.

Authors:  Junjia Liu; T Aaron Bedell; Julian G West; Erik J Sorensen
Journal:  Tetrahedron       Date:  2016-01-28       Impact factor: 2.457

Review 10.  Chemical Synthesis of Cell Wall Constituents of Mycobacterium tuberculosis.

Authors:  Mira Holzheimer; Jeffrey Buter; Adriaan J Minnaard
Journal:  Chem Rev       Date:  2021-06-30       Impact factor: 60.622
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