Literature DB >> 16898787

Synthetic studies toward the bryostatins: a substrate-controlled approach to the A-ring.

Gary E Keck1, Dennie S Welch, Paige K Vivian.   

Abstract

[reaction: see text] The synthesis of a C1-C13 A-ring subunit of bryostatin 1 is detailed. The key features of the approach include the convergent fragment assembly with a highly stereoselective construction of the C7-C8 bond indicated above.

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Year:  2006        PMID： 16898787      PMCID： PMC2516405          DOI： 10.1021/ol061173h

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


  19 in total

1.  New, abridged pathway to Masamune's "southern hemisphere" intermediate for the total synthesis of bryostatin 7.

Authors:  Karl J Hale; Mark Frigerio; Soraya Manaviazar
Journal:  Org Lett       Date:  2003-02-20       Impact factor: 6.005

2.  The practical synthesis of a novel and highly potent analogue of bryostatin.

Authors:  Paul A Wender; Jeremy L Baryza; Chad E Bennett; F Christopher Bi; Stacey E Brenner; Michael O Clarke; Joshua C Horan; Cindy Kan; Emmanuel Lacôte; Blaise Lippa; Peter G Nell; Tim M Turner
Journal:  J Am Chem Soc       Date:  2002-11-20       Impact factor: 15.419

Review 3.  The chemistry and biology of the bryostatin antitumour macrolides.

Authors:  Karl J Hale; Marc G Hummersone; Soraya Manaviazar; Mark Frigerio
Journal:  Nat Prod Rep       Date:  2002-08       Impact factor: 13.423

4.  A concise, selective synthesis of the polyketide spacer domain of a potent bryostatin analogue.

Authors:  Paul A Wender; Alexander V W Mayweg; Christopher L VanDeusen
Journal:  Org Lett       Date:  2003-02-06       Impact factor: 6.005

5.  Synthetic studies on the bryostatins: preparation of a truncated BC-ring intermediate by pyran annulation.

Authors:  Gary E Keck; Anh P Truong
Journal:  Org Lett       Date:  2005-05-26       Impact factor: 6.005

6.  Bryostatin 1 down-regulates mdr1 and potentiates vincristine cytotoxicity in diffuse large cell lymphoma xenografts.

Authors:  A M Al-Katib; M R Smith; W S Kamanda; G R Pettit; M Hamdan; A N Mohamed; B Chelladurai; R M Mohammad
Journal:  Clin Cancer Res       Date:  1998-05       Impact factor: 12.531

7.  The exceptional chelating ability of dimethylaluminum chloride and methylaluminum dichloride. The merged stereochemical impact of alpha- and beta-stereocenters in chelate-controlled carbonyl addition reactions with enolsilane and hydride nucleophiles.

Authors:  D A Evans; B D Allison; M G Yang; C E Masse
Journal:  J Am Chem Soc       Date:  2001-11-07       Impact factor: 15.419

8.  Pyran annulation: asymmetric synthesis of 2,6-disubstituted-4-methylene tetrahydropyrans.

Authors:  Gary E Keck; Jonathan A Covel; Tobias Schiff; Tao Yu
Journal:  Org Lett       Date:  2002-04-04       Impact factor: 6.005

9.  Therapeutic effects of PKC activators in Alzheimer's disease transgenic mice.

Authors:  René Etcheberrigaray; Mathew Tan; Ilse Dewachter; Cuno Kuipéri; Ingrid Van der Auwera; Stefaan Wera; Lixin Qiao; Barry Bank; Thomas J Nelson; Alan P Kozikowski; Fred Van Leuven; Daniel L Alkon
Journal:  Proc Natl Acad Sci U S A       Date:  2004-07-19       Impact factor: 11.205

10.  Total synthesis of (+/-)-trachyspic acid and determination of the relative configuration.

Authors:  Kanako Hirai; Hidenori Ooi; Tomoyuki Esumi; Yoshiharu Iwabuchi; Susumi Hatakeyama
Journal:  Org Lett       Date:  2003-03-20       Impact factor: 6.005
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  11 in total

1.  Synthesis of a ring-expanded bryostatin analogue.

Authors:  Barry M Trost; Hanbiao Yang; Oliver R Thiel; Alison J Frontier; Cheyenne S Brindle
Journal:  J Am Chem Soc       Date:  2007-02-06       Impact factor: 15.419

2.  A new construction of 2-alkoxypyrans by an acylation-reductive cyclization sequence.

Authors:  Lars V Heumann; Gary E Keck
Journal:  Org Lett       Date:  2007-04-12       Impact factor: 6.005

3.  Substitution on the A-ring confers to bryopyran analogues the unique biological activity characteristic of bryostatins and distinct from that of the phorbol esters.

Authors:  Gary E Keck; Yam B Poudel; Dennie S Welch; Matthew B Kraft; Anh P Truong; Jeffrey C Stephens; Noemi Kedei; Nancy E Lewin; Peter M Blumberg
Journal:  Org Lett       Date:  2009-02-05       Impact factor: 6.005

4.  Convergent assembly of highly potent analogues of bryostatin 1 via pyran annulation: bryostatin look-alikes that mimic phorbol ester function.

Authors:  Gary E Keck; Matthew B Kraft; Anh P Truong; Wei Li; Carina C Sanchez; Noemi Kedei; Nancy E Lewin; Peter M Blumberg
Journal:  J Am Chem Soc       Date:  2008-05-02       Impact factor: 15.419

5.  Synthesis and Biological Evaluation of Fluorescent Bryostatin Analogues.

Authors:  Thomas J Cummins; Noemi Kedei; Agnes Czikora; Nancy E Lewin; Sharon Kirk; Mark E Petersen; Kevin M McGowan; Jin-Qiu Chen; Xiaoling Luo; Randall C Johnson; Sarangan Ravichandran; Peter M Blumberg; Gary E Keck
Journal:  Chembiochem       Date:  2018-03-25       Impact factor: 3.164

6.  Synthetic Studies Toward Bryostatin 1: Preparation of a C(1)-C(16) Fragment by Pyran Annulation.

Authors:  Gary E Keck; Dennie S Welch; Yam B Poudel
Journal:  Tetrahedron Lett       Date:  2006-11-20       Impact factor: 2.415

7.  Molecular modeling, total synthesis, and biological evaluations of C9-deoxy bryostatin 1.

Authors:  Gary E Keck; Yam B Poudel; Arnab Rudra; Jeffrey C Stephens; Noemi Kedei; Nancy E Lewin; Megan L Peach; Peter M Blumberg
Journal:  Angew Chem Int Ed Engl       Date:  2010-06-21       Impact factor: 15.336

8.  Total synthesis of epothilones B and D: stannane equivalents for beta-keto ester dianions.

Authors:  Gary E Keck; Robert L Giles; Victor J Cee; Carrie A Wager; Tao Yu; Matthew B Kraft
Journal:  J Org Chem       Date:  2008-12-19       Impact factor: 4.354

9.  Asymmetric synthesis of (-)-incarvillateine employing an intramolecular alkylation via Rh-catalyzed olefinic C-H bond activation.

Authors:  Andy S Tsai; Robert G Bergman; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2008-04-29       Impact factor: 15.419

10.  Concise synthesis of the bryostatin A-ring via consecutive C-C bond forming transfer hydrogenations.

Authors:  Yu Lu; Michael J Krische
Journal:  Org Lett       Date:  2009-07-16       Impact factor: 6.005
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