Literature DB >> 20932022

Total synthesis of (-)-nakadomarin A.

Mark G Nilson1, Raymond L Funk.   

Abstract

A concise diastereoselective total synthesis of (-)-nakadomarin A has been completed in 21 steps from D-pyroglutamic acid. Key steps include an enecarbamate Michael addition/furan-N-acyliminium ion cascade cyclization to provide the tetracyclic core and ring-closing alkyne and alkene metatheses to construct the fifteen- and eight-membered azacycles, respectively.

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Year:  2010        PMID： 20932022      PMCID： PMC3151009          DOI： 10.1021/ol102079z

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


  15 in total

1.  Formal synthesis of (+)-nakadomarin A.

Authors:  Fuyuhiko Inagaki; Masahiko Kinebuchi; Naoki Miyakoshi; Chisato Mukai
Journal:  Org Lett       Date:  2010-04-16       Impact factor: 6.005

2.  A fine-tuned molybdenum hexacarbonyl/phenol initiator for alkyne metathesis.

Authors:  Volodymyr Sashuk; Jolanta Ignatowska; Karol Grela
Journal:  J Org Chem       Date:  2004-10-29       Impact factor: 4.354

3.  Total synthesis of (-)-nakadomarin A.

Authors:  Pavol Jakubec; Dane M Cockfield; Darren J Dixon
Journal:  J Am Chem Soc       Date:  2009-11-25       Impact factor: 15.419

4.  The first example of Nazarov reactions of vinyl cumulenyl ketones.

Authors:  Eric Leclerc; Marcus A Tius
Journal:  Org Lett       Date:  2003-04-17       Impact factor: 6.005

5.  Practical new silyloxy-based alkyne metathesis catalysts with optimized activity and selectivity profiles.

Authors:  Johannes Heppekausen; Robert Stade; Richard Goddard; Alois Fürstner
Journal:  J Am Chem Soc       Date:  2010-08-18       Impact factor: 15.419

Review 6.  Alkyne metathesis.

Authors:  Alois Furstner; Paul W Davies
Journal:  Chem Commun (Camb)       Date:  2005-02-28       Impact factor: 6.222

7.  Indenylidene complexes of ruthenium: optimized synthesis, structure elucidation, and performance as catalysts for olefin metathesis--application to the synthesis of the ADE-ring system of nakadomarin A.

Authors:  A Fürstner; O Guth; A Düffels; G Seidel; M Liebl; B Gabor; R Mynott
Journal:  Chemistry       Date:  2001-11-19       Impact factor: 5.236

8.  The first total synthesis of nakadomarin A.

Authors:  Toshiaki Nagata; Masako Nakagawa; Atsushi Nishida
Journal:  J Am Chem Soc       Date:  2003-06-25       Impact factor: 15.419

9.  Expedient synthesis of the tetracyclic core of ent-nakadomarin A.

Authors:  Haibing Deng; Xiaobao Yang; Zhaolong Tong; Zhong Li; Hongbin Zhai
Journal:  Org Lett       Date:  2008-04-08       Impact factor: 6.005

10.  A concise asymmetric synthesis of the ADE fragment of nakadomarin A.

Authors:  Kateri A Ahrendt; Robert M Williams
Journal:  Org Lett       Date:  2004-11-25       Impact factor: 6.005
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  11 in total

1.  STUDIES DIRECTED TOWARD THE SYNTHESIS OF NAKADOMARIN A.

Authors:  Thomas Haimowitz; Mark E Fitzgerald; Jeffrey D Winkler
Journal:  Tetrahedron Lett       Date:  2011-04-27       Impact factor: 2.415

2.  A versatile enantioselective synthesis of azabicyclic ring systems: a concise total synthesis of (+)-grandisine D and unnatural analogues.

Authors:  Olugbeminiyi O Fadeyi; Timothy J Senter; Kristopher N Hahn; Craig W Lindsley
Journal:  Chemistry       Date:  2012-03-30       Impact factor: 5.236

3.  A Highly Efficient Synthesis of Z-Macrocycles Using Stereoretentive, Ruthenium-Based Metathesis Catalysts.

Authors:  Tonia S Ahmed; Robert H Grubbs
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-12       Impact factor: 15.336

4.  A General, Enantioselective Synthesis of 1-Azabicyclo[m.n.0]alkane Ring Systems.

Authors:  Timothy J Senter; Michael L Schulte; Leah C Konkol; Tyler E Wadzinski; Craig W Lindsley
Journal:  Tetrahedron Lett       Date:  2013-03-27       Impact factor: 2.415

5.  Efficient and selective formation of macrocyclic disubstituted Z alkenes by ring-closing metathesis (RCM) reactions catalyzed by Mo- or W-based monoaryloxide pyrrolide (MAP) complexes: applications to total syntheses of epilachnene, yuzu lactone, ambrettolide, epothilone C, and nakadomarin A.

Authors:  Chenbo Wang; Miao Yu; Andrew F Kyle; Pavol Jakubec; Darren J Dixon; Richard R Schrock; Amir H Hoveyda
Journal:  Chemistry       Date:  2013-01-23       Impact factor: 5.236

6.  Synthesis of macrocyclic natural products by catalyst-controlled stereoselective ring-closing metathesis.

Authors:  Miao Yu; Chenbo Wang; Andrew F Kyle; Pavol Jakubec; Darren J Dixon; Richard R Schrock; Amir H Hoveyda
Journal:  Nature       Date:  2011-11-02       Impact factor: 49.962

7.  Evolution of catalytic stereoselective olefin metathesis: from ancillary transformation to purveyor of stereochemical identity.

Authors:  Amir H Hoveyda
Journal:  J Org Chem       Date:  2014-04-10       Impact factor: 4.354

8.  Synthetic Studies Towards the Core Structure of Nakadomarin A by a Thioamide-Based Strategy.

Authors:  Jai K Chavda; Panayiotis A Procopiou; Peter N Horton; Simon J Coles; Michael J Porter
Journal:  European J Org Chem       Date:  2013-11-14

9.  "Canopy Catalysts" for Alkyne Metathesis: Molybdenum Alkylidyne Complexes with a Tripodal Ligand Framework.

Authors:  Julius Hillenbrand; Markus Leutzsch; Ektoras Yiannakas; Christopher P Gordon; Christian Wille; Nils Nöthling; Christophe Copéret; Alois Fürstner
Journal:  J Am Chem Soc       Date:  2020-06-09       Impact factor: 15.419

10.  Total Synthesis Provides Strong Evidence: Xestocyclamine A is the Enantiomer of Ingenamine.

Authors:  Zhanchao Meng; Alois Fürstner
Journal:  J Am Chem Soc       Date:  2020-06-23       Impact factor: 15.419
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