Literature DB >> 18767800

Synthesis of hydroxylated bicyclic amino acids from L-tyrosine: octahydro-1H-indole carboxylates.

Joshua G Pierce1, Dhanalakshmi Kasi, Makoto Fushimi, Anthony Cuzzupe, Peter Wipf.   

Abstract

A stereoselective approach to polyhydroxylated L-Choi derivatives has been developed. The oxidative cyclization of L-tyrosine was optimized to avoid partial racemization and to allow a more efficient scale-up.

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Year:  2008        PMID： 18767800      PMCID： PMC2739982          DOI： 10.1021/jo801552j

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  23 in total

1.  [ON THE COMPOSITION OF PARKACIN].

Authors:  W DOEPKE
Journal:  Arch Pharm Ber Dtsch Pharm Ges       Date:  1963-11

2.  Enantioselective syntheses of aeruginosin 298-A and its analogues using a catalytic asymmetric phase-transfer reaction and epoxidation.

Authors:  Takashi Ohshima; Vijay Gnanadesikan; Tomoyuki Shibuguchi; Yuhei Fukuta; Tetsuhiro Nemoto; Masakatsu Shibasaki
Journal:  J Am Chem Soc       Date:  2003-09-17       Impact factor: 15.419

3.  Design, synthesis, and evaluation of octahydropyranopyrrole-based inhibitors of mammalian ribonucleotide reductase.

Authors:  Michael J Fuertes; Jaskiran Kaur; Prasant Deb; Barry S Cooperman; Amos B Smith
Journal:  Bioorg Med Chem Lett       Date:  2005-09-19       Impact factor: 2.823

4.  Aeruginosin 103-A, a thrombin inhibitor from the cyanobacterium Microcystis viridis.

Authors:  S Kodani; K Ishida; M Murakami
Journal:  J Nat Prod       Date:  1998-08       Impact factor: 4.050

5.  Dysinosin A: a novel inhibitor of Factor VIIa and thrombin from a new genus and species of Australian sponge of the family Dysideidae.

Authors:  Anthony R Carroll; Gregory K Pierens; Greg Fechner; Priscila De Almeida Leone; Anna Ngo; Moana Simpson; Edward Hyde; John N A Hooper; Stig-Lennart Boström; Djordje Musil; Ronald J Quinn
Journal:  J Am Chem Soc       Date:  2002-11-13       Impact factor: 15.419

6.  1,3-dipolar cycloaddition chemistry for the preparation of novel indolizinone-based compounds.

Authors:  Edwin M Mmutlane; Joel M Harris; Albert Padwa
Journal:  J Org Chem       Date:  2005-09-30       Impact factor: 4.354

7.  Synthesis and pharmacological evaluation of novel octahydro-1H-pyrido[1,2-a]pyrazine as mu-opioid receptor antagonists.

Authors:  Bertrand Le Bourdonnec; Allan J Goodman; Thomas M Graczyk; Serge Belanger; Pamela R Seida; Robert N DeHaven; Roland E Dolle
Journal:  J Med Chem       Date:  2006-12-14       Impact factor: 7.446

8.  Synthesis of a ring-oxygenated variant of the 2-carboxy-6-hydroxyoctahydroindole core of aeruginosin 298-A from glucose.

Authors:  Xiaoping Nie; Guijun Wang
Journal:  J Org Chem       Date:  2005-10-28       Impact factor: 4.354

9.  The N-acyloxyiminium ion aza-Prins route to octahydroindoles: total synthesis and structural confirmation of the antithrombotic marine natural product oscillarin.

Authors:  Stephen Hanessian; Martin Tremblay; Jens F W Petersen
Journal:  J Am Chem Soc       Date:  2004-05-19       Impact factor: 15.419

10.  Structure-based organic synthesis of unnatural aeruginosin hybrids as potent inhibitors of thrombin.

Authors:  Stephen Hanessian; Karolina Ersmark; Xiaotian Wang; Juan R Del Valle; Niklas Blomberg; Yafeng Xue; Ola Fjellström
Journal:  Bioorg Med Chem Lett       Date:  2007-03-27       Impact factor: 2.823
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  4 in total

1.  Exploring the structure-activity relationships of ABCC2 modulators using a screening approach.

Authors:  Gloria Wissel; Pavel Kudryavtsev; Leo Ghemtio; Päivi Tammela; Peter Wipf; Marjo Yliperttula; Moshe Finel; Arto Urtti; Heidi Kidron; Henri Xhaard
Journal:  Bioorg Med Chem       Date:  2015-04-17       Impact factor: 3.641

2.  Synthesis and biological evaluation of epidithio-, epitetrathio-, and bis-(methylthio)diketopiperazines: synthetic methodology, enantioselective total synthesis of epicoccin G, 8,8'-epi-ent-rostratin B, gliotoxin, gliotoxin G, emethallicin E, and haematocin and discovery of new antiviral and antimalarial agents.

Authors:  K C Nicolaou; Min Lu; Sotirios Totokotsopoulos; Philipp Heretsch; Denis Giguère; Ya-Ping Sun; David Sarlah; Thu H Nguyen; Ian C Wolf; Donald F Smee; Craig W Day; Selina Bopp; Elizabeth A Winzeler
Journal:  J Am Chem Soc       Date:  2012-10-04       Impact factor: 15.419

3.  Synthesis and chemical diversity analysis of bicyclo[3.3.1]non-3-en-2-ones.

Authors:  Jared T Hammill; Julia Contreras-García; Aaron M Virshup; David Beratan; Weitao Yang; Peter Wipf
Journal:  Tetrahedron       Date:  2010-03-31       Impact factor: 2.457

4.  A microwave assisted intramolecular-furan-Diels-Alder approach to 4-substituted indoles.

Authors:  Filip Petronijevic; Cody Timmons; Anthony Cuzzupe; Peter Wipf
Journal:  Chem Commun (Camb)       Date:  2008-11-11       Impact factor: 6.222
  4 in total

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