Literature DB >> 20462232

Enantioselective synthesis of (+)-isolysergol via ring-closing metathesis.

Jason A Deck1, Stephen F Martin.   

Abstract

The first enantioselective synthesis of (+)-isolysergol was completed in 12 steps from commercially available materials by a novel approach that features a late stage microwave-mediated, diastereomeric ring-closing metathesis catalyzed by a chiral molybdenum catalyst to simultaneously form the D ring and set the stereocenter at C(8).

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Year:  2010        PMID： 20462232      PMCID： PMC2879020          DOI： 10.1021/ol100819f

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


  14 in total

1.  Concise formal synthesis of (-)-peduncularine via ring-closing metathesis.

Authors:  David G Washburn; Richard W Heidebrecht; Stephen F Martin
Journal:  Org Lett       Date:  2003-09-18       Impact factor: 6.005

2.  Formal syntheses of (+/-)-pinnaic acid and (+/-)-halichlorine.

Authors:  Rodrigo B Andrade; Stephen F Martin
Journal:  Org Lett       Date:  2005-12-08       Impact factor: 6.005

3.  Synthesis of 10alpha-methoxy-delta8,9-lysergaldehyde from elymoclavine.

Authors:  T C Choong; B L Thompson; H R Shough
Journal:  J Pharm Sci       Date:  1977-09       Impact factor: 3.534

4.  Biosynthesis of ergot alkaloids. Synthesis of 6-methyl-8-acetoxymethylene-9-ergolene and its incorporation into ergotoxine by Claviceps.

Authors:  C C Lin; G E Blair; J M Cassady; D Gröger; W Maier; H G Floss
Journal:  J Org Chem       Date:  1973-06-15       Impact factor: 4.354

5.  General strategy for the syntheses of corynanthe, tacaman, and oxindole alkaloids.

Authors:  Alexander Deiters; Martin Pettersson; Stephen F Martin
Journal:  J Org Chem       Date:  2006-08-18       Impact factor: 4.354

Review 6.  Progress and prospects of ergot alkaloid research.

Authors:  J Mukherjee; M Menge
Journal:  Adv Biochem Eng Biotechnol       Date:  2000       Impact factor: 2.635

7.  Total synthesis of (+/-)-lysergic acid, lysergol, and isolysergol by palladium-catalyzed domino cyclization of amino allenes bearing a bromoindolyl group.

Authors:  Shinsuke Inuki; Shinya Oishi; Nobutaka Fujii; Hiroaki Ohno
Journal:  Org Lett       Date:  2008-10-29       Impact factor: 6.005

8.  Synthesis of bridged azabicyclic structures via ring-closing olefin metathesis.

Authors:  Christopher E Neipp; Stephen F Martin
Journal:  J Org Chem       Date:  2003-11-14       Impact factor: 4.354

9.  Toward the total synthesis of FR901483: concise synthesis of the azatricyclic skeleton.

Authors:  Suvi T M Simila; Stephen F Martin
Journal:  J Org Chem       Date:  2007-06-08       Impact factor: 4.354

10.  A new synthesis of lysergic acid.

Authors:  James B Hendrickson; Jian Wang
Journal:  Org Lett       Date:  2004-01-08       Impact factor: 6.005
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  8 in total

1.  Total synthesis of dihydrolysergic acid and dihydrolysergol: development of a divergent synthetic strategy applicable to rapid assembly of D-ring analogs.

Authors:  Kiyoun Lee; Yam B Poudel; Christopher M Glinkerman; Dale L Boger
Journal:  Tetrahedron       Date:  2015-09-02       Impact factor: 2.457

2.  Novel approach to the lundurine alkaloids: synthesis of the tetracyclic core.

Authors:  Suvi T M Orr; Jianhua Tian; Meike Niggemann; Stephen F Martin
Journal:  Org Lett       Date:  2011-09-02       Impact factor: 6.005

3.  Natural Products and Their Mimics as Targets of Opportunity for Discovery.

Authors:  Stephen F Martin
Journal:  J Org Chem       Date:  2017-09-15       Impact factor: 4.354

4.  Synthesis of (±)-tetrapetalone A-Me aglycon.

Authors:  Peter N Carlsen; Tyler J Mann; Amir H Hoveyda; Alison J Frontier
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-07       Impact factor: 15.336

5.  Facile Syntheses of Substituted, Conformationally-Constrained Benzoxazocines and Benzazocines via Sequential Multicomponent Assembly and Cyclization.

Authors:  James J Sahn; Stephen F Martin
Journal:  Tetrahedron Lett       Date:  2011-12-21       Impact factor: 2.415

6.  Concise total synthesis of (+/-)-pseudotabersonine via double ring-closing metathesis strategy.

Authors:  Bo Cheng; James D Sunderhaus; Stephen F Martin
Journal:  Org Lett       Date:  2010-08-20       Impact factor: 6.005

7.  Applications of Ring Closing Metathesis. Total Synthesis of (±)-Pseudotabersonine.

Authors:  Bo Cheng; James D Sunderhaus; Stephen F Martin
Journal:  Tetrahedron       Date:  2015-09-30       Impact factor: 2.457

8.  Palladium-Catalyzed Aminocyclization-Coupling Cascades: Preparation of Dehydrotryptophan Derivatives and Computational Study.

Authors:  Belén Vaz; Claudio Martínez; Francisco Cruz; J Gabriel Denis; Ángel R de Lera; José M Aurrecoechea; Rosana Álvarez
Journal:  J Org Chem       Date:  2021-06-14       Impact factor: 4.354
  8 in total

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