Literature DB >> 15226504

Synthesis of the thapsigargins.

Steven V Ley1, Alessandra Antonello, Emily P Balskus, David T Booth, Søren B Christensen, Ed Cleator, Helen Gold, Klemens Högenauer, Udo Hünger, Rebecca M Myers, Steven F Oliver, Oliver Simic, Martin D Smith, Helmer Søhoel, Alison J A Woolford.   

Abstract

The thapsigargins are a family of complex guaianolides with potent and selective Ca(2+)-modulating properties. This article documents the evolution of a synthetic route through several iterations to a final practical and scaleable synthetic route capable of generating both unnatural and natural products based around the guaianolide skeleton.

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Year:  2004        PMID: 15226504      PMCID: PMC514437          DOI: 10.1073/pnas.0403300101

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN: 0027-8424            Impact factor:   11.205


  12 in total

1.  A route to the thapsigargins from (S)-carvone providing a substrate-controlled total synthesis of trilobolide, nortrilobolide, and thapsivillosin F.

Authors:  Steven F Oliver; Klemens Högenauer; Oliver Simic; Alessandra Antonello; Martin D Smith; Steven V Ley
Journal:  Angew Chem Int Ed Engl       Date:  2003-12-15       Impact factor: 15.336

Review 2.  Sesquiterpenoids from Thapsia species and medicinal chemistry of the thapsigargins.

Authors:  S B Christensen; A Andersen; U W Smitt
Journal:  Fortschr Chem Org Naturst       Date:  1997

3.  Design, synthesis, and pharmacological evaluation of thapsigargin analogues for targeting apoptosis to prostatic cancer cells.

Authors:  C M Jakobsen; S R Denmeade; J T Isaacs; A Gady; C E Olsen; S B Christensen
Journal:  J Med Chem       Date:  2001-12-20       Impact factor: 7.446

4.  Thapsigargine and thapsigargicine, two new histamine liberators from Thapsia garganica L.

Authors:  U Rasmussen; S Brøogger Christensen; F Sandberg
Journal:  Acta Pharm Suec       Date:  1978

5.  Thapsigargin analogues for targeting programmed death of androgen-independent prostate cancer cells.

Authors:  S B Christensen; A Andersen; H Kromann; M Treiman; B Tombal; S Denmeade; J T Isaacs
Journal:  Bioorg Med Chem       Date:  1999-07       Impact factor: 3.641

6.  Prostate-specific antigen-activated thapsigargin prodrug as targeted therapy for prostate cancer.

Authors:  Samuel R Denmeade; Carsten M Jakobsen; Samuel Janssen; Saeed R Khan; Elizabeth S Garrett; Hans Lilja; S Brogger Christensen; John T Isaacs
Journal:  J Natl Cancer Inst       Date:  2003-07-02       Impact factor: 13.506

7.  A conformational mechanism for formation of a dead-end complex by the sarcoplasmic reticulum ATPase with thapsigargin.

Authors:  Y Sagara; J B Wade; G Inesi
Journal:  J Biol Chem       Date:  1992-01-15       Impact factor: 5.157

8.  Thapsigargin discriminates strongly between Ca(2+)-ATPase phosphorylated intermediates with different subcellular distributions in bovine adrenal chromaffin cells.

Authors:  C Caspersen; M Treiman
Journal:  FEBS Lett       Date:  1995-12-11       Impact factor: 4.124

9.  On the mechanism of histamine release induced by thapsigargin from Thapsia garganica L.

Authors:  S A Patkar; U Rasmussen; B Diamant
Journal:  Agents Actions       Date:  1979-04

10.  The role of calcium, pH, and cell proliferation in the programmed (apoptotic) death of androgen-independent prostatic cancer cells induced by thapsigargin.

Authors:  Y Furuya; P Lundmo; A D Short; D L Gill; J T Isaacs
Journal:  Cancer Res       Date:  1994-12-01       Impact factor: 12.701

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  15 in total

1.  An allenic Pauson-Khand approach to 6,12-guaianolides.

Authors:  Francois Grillet; Chaofeng Huang; Kay M Brummond
Journal:  Org Lett       Date:  2011-11-09       Impact factor: 6.005

Review 2.  Development of Anticancer Agents from Plant-Derived Sesquiterpene Lactones.

Authors:  Yulin Ren; Jianhua Yu; A Douglas Kinghorn
Journal:  Curr Med Chem       Date:  2016       Impact factor: 4.530

3.  Blockade of Oncogenic NOTCH1 with the SERCA Inhibitor CAD204520 in T Cell Acute Lymphoblastic Leukemia.

Authors:  Matteo Marchesini; Andrea Gherli; Anna Montanaro; Laura Patrizi; Claudia Sorrentino; Luca Pagliaro; Chiara Rompietti; Samuel Kitara; Sabine Heit; Claus E Olesen; Jesper V Møller; Monia Savi; Leonardo Bocchi; Rocchina Vilella; Federica Rizzi; Marilena Baglione; Giorgia Rastelli; Caterina Loiacono; Roberta La Starza; Cristina Mecucci; Kimberly Stegmaier; Franco Aversa; Donatella Stilli; Anne-Marie Lund Winther; Paolo Sportoletti; Maike Bublitz; William Dalby-Brown; Giovanni Roti
Journal:  Cell Chem Biol       Date:  2020-05-07       Impact factor: 8.116

4.  Allylative Approaches to the Synthesis of Complex Guaianolide Sesquiterpenes from Apiaceae and Asteraceae.

Authors:  Xirui Hu; Andrew J Musacchio; Xingyu Shen; Yujia Tao; Thomas J Maimone
Journal:  J Am Chem Soc       Date:  2019-09-06       Impact factor: 15.419

5.  Discovery of novel SERCA inhibitors by virtual screening of a large compound library.

Authors:  Christopher Elam; Michael Lape; Joel Deye; Jodie Zultowsky; David T Stanton; Stefan Paula
Journal:  Eur J Med Chem       Date:  2011-02-25       Impact factor: 6.514

6.  A Double Allylation Strategy for Gram-Scale Guaianolide Production: Total Synthesis of (+)-Mikanokryptin.

Authors:  Xirui Hu; Silong Xu; Thomas J Maimone
Journal:  Angew Chem Int Ed Engl       Date:  2017-01-03       Impact factor: 15.336

7.  Design, synthesis, and biological evaluation of hydroquinone derivatives as novel inhibitors of the sarco/endoplasmic reticulum calcium ATPase.

Authors:  Stefan Paula; Josh Abell; Joel Deye; Christopher Elam; Michael Lape; Justin Purnell; Robert Ratliff; Kelly Sebastian; Jodie Zultowsky; Robert J Kempton
Journal:  Bioorg Med Chem       Date:  2009-08-04       Impact factor: 3.641

8.  Rh(I)-catalyzed cyclocarbonylation of allenol esters to prepare acetoxy 4-alkylidenecyclopent-3-en-2-ones.

Authors:  Kay M Brummond; Matthew M Davis; Chaofeng Huang
Journal:  J Org Chem       Date:  2009-11-06       Impact factor: 4.354

9.  A redox economical synthesis of bioactive 6,12-guaianolides.

Authors:  Bo Wen; Joseph K Hexum; John C Widen; Daniel A Harki; Kay M Brummond
Journal:  Org Lett       Date:  2013-05-10       Impact factor: 6.005

Review 10.  Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin-Anh and Chelation-Control Models.

Authors:  Nicole D Bartolo; Jacquelyne A Read; Elizabeth M Valentín; K A Woerpel
Journal:  Chem Rev       Date:  2020-01-06       Impact factor: 60.622

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