Literature DB >> 19119873

A rapid, asymmetric synthesis of the decahydrofluorene core of the hirsutellones.

S David Tilley1, Keith P Reber, Erik J Sorensen.   

Abstract

A tandem ketene-trapping/Diels-Alder cyclization sequence was the pivotal transformation in an efficient, asymmetric synthesis of a decahydrofluorene tricyclic structure possessing eight stereogenic centers and key features of the hirsutellone class of antitubercular natural products. The hirsutellone-like beta-keto ester that was fashioned by this sequence (13 steps; 6% overall yield) demonstrated significant inhibitory activity against Mycobacterium tuberculosis. The mechanism of action of this antitubercular compound is not yet known.

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Year:  2009        PMID： 19119873      PMCID： PMC3115586          DOI： 10.1021/ol802768p

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


  3 in total

Review 1.  Drugs versus bugs: in pursuit of the persistent predator Mycobacterium tuberculosis.

Authors:  James C Sacchettini; Eric J Rubin; Joel S Freundlich
Journal:  Nat Rev Microbiol       Date:  2008-01       Impact factor: 60.633

2.  Toward the development of a general chiral auxiliary. A total synthesis of (+)-tetronolide via a tandem ketene-trapping [4 + 2] cycloaddition strategy.

Authors:  Robert K Boeckman; Pengcheng Shao; Stephen T Wrobleski; Debra J Boehmler; Geoffrey R Heintzelman; Antonio J Barbosa
Journal:  J Am Chem Soc       Date:  2006-08-16       Impact factor: 15.419

3.  Total synthesis of macquarimicins using an intramolecular Diels-Alder approach inspired by a biosynthetic pathway.

Authors:  Ryosuke Munakata; Hironori Katakai; Tatsuo Ueki; Jun Kurosaka; Ken-Ichi Takao; Kin-Ichi Tadano
Journal:  J Am Chem Soc       Date:  2004-09-15       Impact factor: 15.419
  3 in total
  15 in total

1.  Bioinspired synthesis of hirsutellones A, B, and C.

Authors:  K C Nicolaou; Ya-Ping Sun; David Sarlah; Weiqiang Zhan; T Robert Wu
Journal:  Org Lett       Date:  2011-09-14       Impact factor: 6.005

2.  Preparation of orthogonally protected (2S, 3R)-2-amino-3-methyl-4-phosphonobutyric acid (Pmab) as a phosphatase-stable phosphothreonine mimetic and its use in the synthesis of Polo-box domain-binding peptides.

Authors:  Fa Liu; Jung-Eun Park; Kyung S Lee; Terrence R Burke
Journal:  Tetrahedron       Date:  2009-11-21       Impact factor: 2.457

Review 3.  A brief history of antibiotics and select advances in their synthesis.

Authors:  Kyriacos C Nicolaou; Stephan Rigol
Journal:  J Antibiot (Tokyo)       Date:  2017-07-05       Impact factor: 2.649

4.  Nature-inspired total synthesis of (-)-fusarisetin A.

Authors:  Jing Xu; Eduardo J E Caro-Diaz; Lynnie Trzoss; Emmanuel A Theodorakis
Journal:  J Am Chem Soc       Date:  2012-03-08       Impact factor: 15.419

5.  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

6.  Stereoselective Synthesis of the Decahydrofluorene Core of the Hirsutellones.

Authors:  Geoff T Halvorsen; William R Roush
Journal:  Tetrahedron Lett       Date:  2011-04-27       Impact factor: 2.415

7.  Fusarisetin A: Scalable Total Synthesis and Related Studies.

Authors:  Jing Xu; Eduardo J E Caro-Diaz; Michelle H Lacoske; Chao-I Hung; Colin Jamora; Emmanuel A Theodorakis
Journal:  Chem Sci       Date:  2012-08-23       Impact factor: 9.825

Review 8.  Bond formations by intermolecular and intramolecular trappings of acylketenes and their applications in natural product synthesis.

Authors:  Keith P Reber; S David Tilley; Erik J Sorensen
Journal:  Chem Soc Rev       Date:  2009-09-02       Impact factor: 54.564

9.  Total synthesis of hirsutellone B.

Authors:  K C Nicolaou; David Sarlah; T Robert Wu; Weiqiang Zhan
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  Toward a synthesis of hirsutellone B by the concept of double cyclization.

Authors:  Keith P Reber; S David Tilley; Cheryl A Carson; Erik J Sorensen
Journal:  J Org Chem       Date:  2013-09-23       Impact factor: 4.354
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