Literature DB >> 16402833

Organometallic enantiomeric scaffolding: organometallic chirons. Total synthesis of (-)-Bao Gong Teng A by a molybdenum-mediated [5 + 2] cycloaddition.

Yongqiang Zhang1, Lanny S Liebeskind.   

Abstract

Bao Gong Teng A, an optically active tropane alkaloid with hypotensive and miotic activity isolated from the Chinese herb Erycibe obtusifolia Benth, was synthesized by an "organometallic chiron" strategy in which single enantiomers of TpMo(CO)(2)(eta(3)-pyridinyl) complexes are produced in quantity and then elaborated easily and efficiently to generate, after demetalation, highly enantiopure advanced synthetic intermediates possessing the tropane core.

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Year:  2006        PMID： 16402833     DOI： 10.1021/ja055623x

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  9 in total

1.  Organometallic enantiomeric scaffolding: a strategy for the enantiocontrolled construction of regio- and stereodivergent trisubstituted piperidines from a common precursor.

Authors:  Heilam Wong; Ethel C Garnier-Amblard; Lanny S Liebeskind
Journal:  J Am Chem Soc       Date:  2011-04-22       Impact factor: 15.419

2.  Novel Substitutions of 1-Alkoxy- and 1-Arylsulfonyloxy-η-Allylmolybdenum Complexes. A Case for η-Alkenyl Carbene Complexes as Intermediates.

Authors:  Thomas C Coombs; Wenwei Huang; Ethel C Garnier-Amblard; Lanny S Liebeskind
Journal:  Organometallics       Date:  2010-11-08       Impact factor: 3.876

3.  Organometallic enantiomeric scaffolding. A molybdenum-mediated intramolecular nucleophilic ketalization-demetalation cascade. Total synthesis of (+)-(1R,2S,5S,7R)-2-hydroxy-exo-brevicomin.

Authors:  Bo Cheng; Lanny S Liebeskind
Journal:  Org Lett       Date:  2009-08-20       Impact factor: 6.005

4.  The enantiomeric scaffold approach to highly functionalized 1-oxadecalines: enantio- and regiocontrolled [4 + 2] cycloadditions of 5-alkenyl-eta3-pyranylmolybdenum complexes.

Authors:  Ramón Gómez Arrayás; Jingjun Yin; Lanny S Liebeskind
Journal:  J Am Chem Soc       Date:  2007-02-14       Impact factor: 15.419

5.  Asymmetric Synthesis of (+)-Iso-6-Cassine via Stereoselective Intramolecular Amidomercuration.

Authors:  Satwinder Singh; Om V Singh; Hyunsoo Han
Journal:  Tetrahedron Lett       Date:  2007-11-19       Impact factor: 2.415

6.  Organometallic enantiomeric scaffolding: general access to 2-substituted oxa- and azabicyclo[3.2.1]octenes via a Brønsted acid catalyzed [5 + 2] cycloaddition reaction.

Authors:  Ethel C Garnier; Lanny S Liebeskind
Journal:  J Am Chem Soc       Date:  2008-05-15       Impact factor: 15.419

7.  Practical, scalable, high-throughput approaches to eta3-pyranyl and eta3-pyridinyl organometallic enantiomeric scaffolds using the Achmatowicz reaction.

Authors:  Thomas C Coombs; Maurice D Lee; Heilam Wong; Matthew Armstrong; Bo Cheng; Wenyong Chen; Alessandro F Moretto; Lanny S Liebeskind
Journal:  J Org Chem       Date:  2008-01-03       Impact factor: 4.354

8.  Organometallic enantiomeric scaffolding. Sequential semipinacol/1,5-"Michael-like" reactions as a strategic approach to bridgehead-quaternary center aza[3.3.1]bicyclics: application to the total synthesis of (-)-adaline.

Authors:  Thomas C Coombs; Yongqiang Zhang; Ethel C Garnier-Amblard; Lanny S Liebeskind
Journal:  J Am Chem Soc       Date:  2009-01-28       Impact factor: 15.419

9.  A new reaction motif: "homo-S(N)2'-like" direct nucleophilic addition to neutral eta(3)-allylmolybdenum complexes. total synthesis of the antimalarial (+)-isofebrifugine.

Authors:  Wenyong Chen; Lanny S Liebeskind
Journal:  J Am Chem Soc       Date:  2009-09-09       Impact factor: 15.419
  9 in total

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